Pyridine-N-oxide-substituted salicylaldehyde or salicyclic acid derivatives, their preparation and their use as herbicides

ABSTRACT

Pyridine-N-oxide-substituted salicylaldehyde and salicylic acid derivatives of the general formula I ##STR1## where R is a formyl group, a CO 2  H group or a radical which can be hydrolyzed to CO 2  H and the other substituents have the following meanings: 
     R 2  is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; 
     X is nitrogen or CR 13 , R 13  being hydrogen or halogen or together with R 3  forming a 3- to 4-membered alkylene or alkenylene chain in which at least one methylene group is replaced by oxygen; 
     R 3  is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, or R 3  is linked with R 13  as indicated above to give a 5- or 6-membered ring; 
     Y is oxygen or sulfur; 
     R 14  -R 17  are an unsubstituted or alkyl-substituted cycloalkyl group; an unsubstituted or substituted alkyl group; an unsubstituted or substituted alkoxy or alkylthio group; a dialkylamino group or a dialkylaminoxy group; an unsubstituted or substituted alkenyl or alkynyl group, hydrogen, halogen, nitro or cyano, 
     are described.

The present invention relates to pyridine-N-oxide-substituted salicylaldehyde and salicylic acid derivatives of the general formula I ##STR2## where R is a formyl group, a CO₂ H group or a radical which can be hydrolyzed to give CO₂ H and the other substituents have the following meanings:

R² is halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio;

X is nitrogen or CR¹³, R¹³ being hydrogen or halogen or together with R³ forming a 3- to 4-membered alkylene or alkenylene chain in which one methylene group in each case is replaced by oxygen;

R³ is halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio, or R³ is linked with R¹³ as indicated above to give a 5- or 6-membered ring;

Y is oxygen or sulfur;

R¹⁴ -R¹⁷ are

a) a C₃ -C₈ -cycloalkyl group, which can carry one to three C₁ -C₄ -alkyl radicals;

b) a C₁ -C₈ -alkyl group, a C₁ -C₈ -alkoxy group or a C₁ -C₄ -alkylthio group, the groups mentioned in each case being able to carry one to five halogen atoms and/or one of the following radicals:

C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, cyano, C₃ -C₈ -cycloalkyl or di-C₁ -C₄ -alkylamino;

c) a di-C₁ -C₄ -alkylamino group or a di-C₁ -C₄ -alkylaminoxy group;

d) a C₂ -C₆ -alkenyl group or a C₂ -C₆ -alkynyl group, which can carry one to five halogen atoms and/or one of the following radicals:

C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio;

e) hydrogen, halogen, nitro or cyano.

According to the prior art, eg. WO 91/13065 and DE-A 39 19 435, salicylaldehyde and salicylic acid derivatives having an unsubstituted pyridyl radical show a herbicidal action. The action of the compounds known from the literature is not always satisfactory with respect to herbicidal action, the bioregulatory action and/or selectivity, and it is therefore an object of the invention to make available pyridyl-substituted salicylaldehyde and salicylic acid derivatives having improved action.

We have now found that this object is achieved by the pyridine-N-oxide-substituted derivatives I defined at the outset. The novel compounds I show an excellent herbicidal action with, to some extent, improved selectivity to crop plants.

We have also found processes for preparing the compounds I and their use as herbicides and growth regulators.

The invention furthermore relates to intermediates of the formula IV: ##STR3## where the radicals R¹⁴ -R¹⁷ have the meanings mentioned at the outset and Y, R¹⁸ and R¹⁹ are:

hydrogen;

C₁ -C₄ -alkyl, this radical in each case being able to carry one to five halogen atoms and/or one to two C₁ -C₄ -alkoxy groups;

phenyl, this radical in each case being able to carry one to five halogen atoms and/or one to two of the following groups: C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl or nitro;

additionally the two radicals together are a C₂ -C₆ -alkylene chain, which can be substituted by one to five halogen atoms and/or C₁ -C₄ -alkyl radicals;

Y is an oxygen or sulfur atom.

The invention also relates to intermediates of the formula III ##STR4## where the radicals have the meanings indicated above, and those intermediates of the formula III in which R is COR¹ and R¹ has the meanings indicated above.

In the description, the substituents mentioned below have the preferred following meanings:

C₁ -C₄ -alkyl: methyl, ethyl, 1-propyl, 2-propyl, 2-methyl-2-propyl, 2-methyl-1-propyl, 1-butyl, 2-butyl;

C₁ -C₈ -alkyl: C₁ -C₄ -alkyl and also pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl;

C₁ -C₂ -haloalkyl: fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

C₁ -C₂ -haloalkoxy: difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy and pentafluoroethoxy;

C₁ -C₄ -alkoxy: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, in particular methoxy, ethoxy, 1-methylethoxy;

C₁ -C₄ -alkylthio: methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, in particular methylthio and ethylthio;

C₃ -C₆ -alkenyl: 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl;

C₃ -C₆ -alkynyl: 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

The radical R is widely variable with respect to the radicals which can be hydrolyzed to the carboxyl group. For example, R is a group ##STR5## where R¹ has the following meanings: R¹ is

a) hydrogen;

b) a succinylimidoxy group;

c) a 5-membered heteroaromatic linked via a nitrogen atom, such as pyrrolyl, pyrazolyl, imidazolyl or triazolyl, which can carry one to two halogen atoms, in particular fluorine and chlorine, and/or one to two of the following radicals:

C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl, in particular C₁ -C₂ -haloalkyl; C₁ -C₄ -haloalkoxy, in particular C₁ -C₂ -haloalkoxy; C₁ -C₄ -alkoxy; C₁ -C₄ -alkylthio;

d) R¹ is additionally a radical --(O)_(m) --NR⁶ R⁷, where m is 0 or 1 and R⁶ and R⁷, which can be identical or different, have the following meanings:

hydrogen;

C₁ -C₈ -alkyl, in particular C₁ -C₄ -alkyl;

C₃ -C₆ -alkenyl, in particular 2-propenyl, 2-butenyl, 3-methyl-2-butenyl and 3-methyl-2-pentenyl;

C₃ -C₆ -alkynyl, preferably 2-propynyl, 2-butynyl, 1-methyl-2-propynyl and 1-methyl-2-butynyl, in particular 2-propynyl;

C₃ -C₈ -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, these alkyl, cycloalkyl, alkenyl and alkynyl groups in each case being able to carry one to five, in particular one to three, halogen atoms, preferably fluorine or chlorine, and/or one to two of the following groups:

C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkenylthio, C₃ -C₆ -alkynyloxy, C₃ -C₆ -alkynylthio, the alkenyl and alkynyl constituents present in these radicals preferably having the abovementioned meanings;

C₁ -C₄ -alkylcarbonyl such as, in particular, methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl;

C₁ -C₄ -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, 1-methylethoxycarbonyl, butyloxycarbonyl, 1-methylpropyloxycarbonyl, 2-methylpropyloxycarbonyl, 1,1-dimethylethoxycarbonyl;

C₃ -C₆ -alkenylcarbonyl, C₃ -C₆ -alkynylcarbonyl, C₃ -C₆ -alkenyloxycarbonyl and C₃ -C₆ -alkynyloxycarbonyl, the alkenyl and alkynyl radicals preferably being defined as above;

phenyl, unsubstituted or mono- or polysubstituted by halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio such as, for example, 2-fluorophenyl, 3-chlorophenyl, 4-bromophenyl, 2-methylphenyl, 3-nitrophenyl, 4-cyanophenyl, 2-trifluoromethylphenyl, 3-methoxyphenyl, 4-trifluoroethoxyphenyl, 2-methylthiophenyl, 2,4-dichlorophenyl, 2-methoxy-3-methylphenyl, 2,4-dimethoxyphenyl, 2-nitro-5-cyanophenyl, 2,6-difluorophenyl;

di-(C₁ -C₄ -alkyl)amino such as, in particular, dimethylamino, diethylamino, dipropylamino, N-propyl-N-methylamino, N-propyl-N-ethylamino, diisopropylamino, N-isopropyl-N-methylamino, N-isopropyl-N-ethylamino, N-isopropyl-N-propylamino;

R⁶ and R⁷ additionally are phenyl, which can be substituted by one or more of the following radicals: halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, in particular C₁ -C₂ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, in particular C₁ -C₂ -haloalkoxy, or C₁ -C₄ -alkylthio;

or R⁶ and R⁷ together form an unsubstituted or substituted C₄ -C₇ -alkylene chain closed to give a ring, which can contain a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, such as --(CH₂)₄ --, --(CH₂)₅ --, --(CH₂)₆ --, --(CH₂)₇ --, --(CH₂)₂ --O--(CH₂)₂ --, --CH₂ --S--(CH₂)₃ --, --(CH₂)₂ --O--(CH₃)₃ --, --NH--(CH₂)₃ --, --CH₂ --NH--(CH₂)₂ --, --CH₂ --CH═CH--CH₂ --, --CH═CH--(CH₂)₃ --, suitable substituents in particular being C₁ -C₄ -alkyl radicals;

e) R¹ is additionally a group ##STR6## where k assumes the values 0, 1 or 2, p assumes the values 1, 2, 3 or 4 and R⁸ is C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl or unsubstituted or substituted phenyl, as mentioned in particular for R⁶ and R⁷ ;

f) R¹ additionally is a radical OR⁹, in which R⁹ is:

i) hydrogen, the cation of an alkali metal or the cation of an alkaline earth metal, such as lithium, sodium, potassium, calcium, magnesium or barium, or an environmentally tolerable organic ammonium ion such as tert-C₁ -C₄ -alkylammonium or ammonium [NH₄ ⁺ ];

ii) C₃ -C₈ -cycloalkyl as mentioned above, which can carry one to three C₁ -C₄ -alkyl groups, in particular cyclopropyl, cyclopentyl, cyclohexyl or methylcyclohexyl;

iii) C₁ -C₈ -alkyl, which can carry one to five halogen atoms, in particular fluorine and chlorine and/or one of the following radicals:

C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, cyano, C₁ -C₄ -alkylcarbonyl, C₃ -C₈ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, phenyl, or phenyl or phenoxy which is mono- or polysubstituted by halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio, in particular as mentioned above;

iv) a C₁ -C₈ -alkyl group, which can carry one to five, preferably one to three, halogen atoms, in particular fluorine and/or chlorine, and carries one of the following radicals: a 5-membered heteroaromatic, containing one to three nitrogen atoms, or a 5-membered heteroaromatic, containing one nitrogen atom and an oxygen or sulfur atom, such as pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, benzotriazolyl, isoxazolyl, oxazolyl or thiazolyl, bonded via a C atom or, if possible, an N atom, the heteroaromatic being able to carry one to four halogen atoms and/or one to two of the following radicals:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, phenyl, C₁ -C₄ -haloalkoxy and/oder C₁ -C₄ -alkylthio. The following may be mentioned in particular: 1-pyrazolyl, 3-methyl-1-pyrazolyl, 4-methyl-1-pyrazolyl, 3,5-dimethyl-1-pyrazolyl, 3-phenyl-1-pyrazolyl, 4-phenyl-1-pyrazolyl, 4-chloro-1-pyrazolyl, 4-bromo-1-pyrazolyl, 1-imidazolyl, 1-benzimidazolyl, 1,2,4-triazol-1-yl, 3-methyl-1,2,4-triazol-1-yl, 5-methyl-1,2,4-triazol-1-yl, 1-benzotriazolyl, 3-isopropylisoxazol-5-yl, 3-methylisoxazol-5-yl, oxazol-2-yl, thiazol-2-yl, imidazol-2-yl, 3-ethylisoxazol-5-yl, 3-phenylisoxazol-5-yl, 3-tert-butylisoxazol-5-yl;

v) a C₂ -C₆ -alkyl group, which in the 2-position carries one of the following radicals: C₁ -C₄ -alkoxyimino, C₃ -C₆ -alkynyloxyimino, C₃ -C₆ -haloalkenyloxyimino, C₃ -C₆ -alkenyloxyimino or benzyloxyimino;

vi) a C₃ -C₆ -alkenyl group or a C₃ -C₆ -alkynyl group, these groups in turn being able to carry one to five halogen atoms;

vii) R⁹ additionally is a phenyl radical, which can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio, in particular as mentioned above;

viii) a 5-membered heteroaromatic linked via a nitrogen atom, containing one to three nitrogen atoms, such as pyrazolyl, imidazolyl, benzimidazolyl, triazolyl or benzotriazolyl, preferably bonded via the 1-position, the heteroaromatic being able to carry one to two halogen atoms and/or one to two of the following radicals:

C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, phenyl, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio. The following may be mentioned in particular: 1-pyrazolyl, 3-methyl-1-pyrazolyl, 4-methyl-1-pyrazolyl, 3,5-dimethyl-1-pyrazolyl, 3-phenyl-1-pyrazolyl, 4-phenyl-1-pyrazolyl, 4-chloro-1-pyrazolyl, 4-bromo-1-pyrazolyl, 1-imidazolyl, 1-benzimidazolyl, 1,2,4-triazol-1-yl, 3-methyl-1,2,4-triazol-1-yl, 5-methyl-1,2,4-triazol-1-yl, 1-benzotriazolyl, 3,4-dichloroimidazol-1-yl;

ix) R⁹ is additionally a group --N═CR¹⁰ R¹¹, in which R¹⁰ and R¹¹, which can be identical or different, are:

C₁ -C₁₂ -alkyl, in particular C₁ -C₈ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl or C₃ -C₈ -cycloalkyl, these radicals being able to carry a C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio radical and/or an unsubstituted or substituted phenyl radical, in particular as mentioned above;

phenyl, which can be substituted by one or more of the following radicals: halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio, these radicals in particular having the meanings mentioned above for R¹ ;

or R¹⁰ and R¹¹ together form a C₃ -C₁₂ -alkylene chain, which can carry one to three C₁ -C₄ -alkyl groups and can contain a heteroatom from the group consisting of oxygen, sulfur and nitrogen, in particular as mentioned in the case of R⁶ and R⁷ ;

g) R¹ is additionally a radical --NH--SO₂ --R¹², in which R¹² is:

C₁ -C₄ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl or C₃ -C₈ -cycloalkyl, in particular as mentioned above for R¹, these radicals being able to carry a C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio radical and/or a phenyl radical as mentioned above;

unsubstituted or substituted phenyl, in particular as mentioned above.

Particularly preferably, R¹ is an OR⁹ group.

With respect to the biological action, active compounds of the formula I are preferred in which the other substituents have the following meanings:

R² is the C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio groups and halogen atoms mentioned specifically for R¹, in particular chlorine, methyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, particularly preferably methoxy;

X is nitrogen or CR¹³, in which

R¹³ is preferably hydrogen or halogen such as fluorine or chlorine, or together with R³ is a 4- to 5-membered alkylene or alkenylene chain, in which one methylene group in each case is replaced by oxygen, such as --CH₂ --CH₂ --O--, --CH═CH--O--, --CH₂ --CH₂ --CH₂ --O--, --CH═CH--CH₂ O--, in particular hydrogen, fluorine and --CH₂ --CH₂ --O--;

R³ is C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, in particular C₁ -C₂ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, in particular C₁ -C₂ -haloalkoxy, C₁ -C₄ -alkylthio groups, in particular chlorine, methyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, particularly preferably methoxy, or is linked with R¹³ as mentioned above to give a 5- or 6-membered ring;

R¹⁴ -R¹⁷ are

a) a C₃ -C₈ -cycloalkyl group, which can carry one to three C₁ -C₄ -alkyl radicals, in particular cyclopropyl, cyclopentyl, cyclohexyl or methylcyclohexyl;

b₁) a C₁ -C₈ -alkyl group, which can carry one to five halogen atoms and/or one of the following radicals:

C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, particularly C₁ -C₂ -haloalkoxy, C₁ -C₄ -alkylthio, cyano, halogen, eg. fluorine or chlorine, C₃ -C₈ -cycloalkyl or di-C₁ -C₄ -alkylamino;

2-methoxyethyl, 2-ethoxyethyl, 2-dimethylaminoethyl, 2-diethylaminoethyl, methoxymethyl, ethoxymethyl, dimethylaminomethyl, diethylaminomethyl, ethyl, isopropyl, n-propyl, trifluoromethyl and methyl are particularly preferred;

b₂) a C₁ -C₈ -alkoxy group, which can carry one to five halogen atoms and/or one of the following radicals:

C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, particularly C₁ -C₂ -haloalkoxy, C₁ -C₄ -alkylthio, cyano, halogen, eg. fluorine or chlorine, C₃ -C₈ -cycloalkyl or di-C₁ -C₄ -alkylamino; 2-methoxyethoxy, 2-ethoxyethoxy, 2-dimethylaminoethoxy, 2-diethylaminoethoxy, methoxymethoxy, ethoxymethoxy, dimethylaminomethoxy, diethylaminomethoxy, 2-methylthioethoxy, 2,2,2-trifluoroethoxy, methoxy, ethoxy, propoxy, 2-propoxy are particularly preferred;

b₃) a C₁ -C₄ -alkylthio group, which can carry one to five halogen atoms and/or one of the following radicals: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, cyano, C₃ -C₈ -cycloalkyl or di-C₁ -C₄ -alkylamino, particularly preferably methylthio, ethylthio, propylthio, 2-propylthio or methoxymethylthio;

c) a di-(C₁ -C₄ -alkyl)amino group or a di-(C₁ -C₄ -alkyl)aminoxy group, particularly preferably dimethylamino, diethylamino, N-methyl-N-ethylamino, diisopropylamino, dipropylamino, dimethylaminoxy, diethylaminoxy;

d) a C₂ -C₆ -alkenyl group or a C₂ -C₆ -alkynyl group, which can carry one to five halogen atoms and/or one of the following radicals:

C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio, particularly preferably vinyl, 2-propenyl, ethynyl, 1-propynyl, 3-propynyl, 3-methoxy-1-propynyl, chloroallyl;

e) hydrogen, halogen such as fluorine, chlorine, bromine or iodine, nitro; particularly preferably hydrogen and halogen such as, in particular, fluorine or chlorine.

Pyridine-N-oxide-substituted salicylaldehyde and salicylic acid derivatives of the formula I as claimed in claim 1, in which at least two of the radicals R¹⁴ to R¹⁷ are hydrogen, are particularly preferred.

Compounds of the formula I are additionally preferred in which R³ is methoxy and X is CH or CF, or in which R³, together with X, forms an OCH₂ CH₂ chain.

With respect to the intended use of the final products I', intermediates of the formula IV are preferred in which R¹⁴ -R¹⁷ and Y have the meanings indicated above as preferred for the active compounds and R¹⁸ and R¹⁹ are:

hydrogen;

C₁ -C₄ -alkyl, this radical in each case being able to carry one to five halogen atoms and/or one to two C₁ -C₄ -alkoxy groups, particularly methyl and ethyl;

phenyl, this radical in each case being able to carry one to five halogen atoms and/or one to two of the following groups: C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl or nitro, particularly phenyl;

additionally the two radicals can together be a C₂ -C₆ -alkylene chain, which can be substituted by one to five halogen atoms and/or C₁ -C₄ -alkyl radicals, particularly butylene or pentylene.

In the case of the intermediates of the formula III, those are preferred in which R and R¹, R¹⁴ -R¹⁷ and Y have the preferred meanings for the active compounds.

The intermediates of the formula IV are obtained, for example, in the way represented in the following reaction scheme: ##STR7## In this reaction scheme

B is trialkylstannyl such as trimethylstannyl, triethylstannyl, tributylstannyl, tripentylstannyl or trihexylstannyl, dihydroxyboranyl, dialkoxyboranyl such as dimethoxyboranyl, diethoxyboranyl, dipropoxyboranyl, diisopropoxyboranyl or dibutoxyboranyl or isomers, or alkylenedioxyboranyl such as ethylenedioxyboranyl or 1,3-propylenedioxyboranyl;

Z is chlorine, bromine, iodine, C₁ -C₄ -haloalkylsulfonyloxy or C₁ -C₄ -alkylsulfonyloxy such as trifluoromethylsulfonyloxy or fluorosulfonyloxy

and the other radicals are the groups described above.

The cyclic acetals IVa can be prepared starting from the corresponding 6-hydroxybenzoic acids (for Y═O) or 6-mercaptobenzoic acids (for Y═S) by reaction with a compound O═CR¹⁸ R¹⁹ in the presence of an acidic catalyst. To bind the water formed in the reaction, a dehydrating agent can be added, such as eg. molecular sieve, acid anhydrides such as eg. trifluoroacetic anhydride or acetic anhydride, sodium sulfate or calcium chloride, if this promotes the conversion. A reactive acetal of the compound O═CR¹⁸ R¹⁹ such as eg. a dimethyl acetal, diethyl acetal, ethylene acetal or propylene acetal is also suitable. Catalysts which are suitable are particularly acidic ion exchangers, protic acids such as eg. toluenesulfonic acid, sulfuric acid, phosphoric acid etc. or Lewis acids such as eg. aluminum chloride, titanium tetrachloride, zinc chloride, calcium chloride, magnesium chloride, tin chlorides etc. Often the water formed or the alcohol formed from the acetal can be removed directly from the reaction mixture by distillation.

If Z is C₁ -C₄ -haloalkylsulfonyloxy, C₁ -C₄ -alkylsulfonyloxy or fluorosulfonyloxy, the hydroxyl compound (Z═OH) can also first be prepared as described above and then converted, for example by reaction with sulfonic anhydrides or sulfonyl halides, to the desired precursors IVa (see Preparation Examples 1a and 1b).

The precursors IVb are obtained particularly advantageously by reaction of compounds IVa with compounds B-Py in the presence of a catalytically active palladium compound. The boron or tin compounds used are either known or can be prepared in a similar way to known compounds.

A catalytically active palladium compound is employed in this process. Any desired palladium salts or complexes are suitable here which are at least partially soluble in the reaction mixture. The oxidation state of the palladium can be 0 or 2. In the case of the palladium salts, suitable counterions, inter alia, are the following: chloride, bromide, iodide, sulfate, acetate, trifluoroacetate, acetylacetonate or hexafluoro-2,4-pentanedionate. Many different palladium complexes can be used. The precondition is only that the ligands on the palladium can be displaced by the substrate under the reaction conditions. Phosphine ligands such as eg. arylalkylphosphines such as, inter alia, methyldiphenylphosphine, isopropyldiphenylphosphine, triarylphosphines such as, inter alia, triphenylphosphine, tritolylphosphine, trixylylphosphine, trihetarylphosphines such as trifurylphosphine or dimeric phosphines are particularly suitable. Olefinic ligands such as, inter alia, dibenzylideneacetone or its salts, cycloocta-1,5-diene or amines such as trialkylamines (eg. triethylamine, tetramethylethylenediamine and N-methylmorpholine) or pyridine are also highly suitable.

The complex used can be employed directly in the reaction. The process can thus be carried out eg. using tetrakistriphenylphosphinepalladium(0), bistriphenylphosphinepalladium dichloride, bistriphenylphosphinepalladium diacetate, a dibenzylideneacetonepalladium(0) complex, tetrakismethyldiphenylphosphinepalladium(0) or bis(1,2-diphenylphosphinoethane)palladium dichloride. A palladium salt and additionally a suitable ligand can also be used which then only form the catalytically active complex in situ. This procedure suggests itself eg. in the case of the abovementioned salts and phosphine ligands such as eg. trifurylphosphine or tritolylphosphine. Palladium complexes such as eg. tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium or 1,5-cyclooctadienepalladium dichloride can also be further activated by the addition of ligands such as eg. trifurylphosphine or tritolylphosphine.

Customarily, from 0.001 to 10 mol %, in particular from 0.005 to 5 mol %, of the palladium compound (salt or complex) are used, based on the compound B-Py. Higher amounts are possible but more uneconomical.

The amount of B-Py, based on the starting substance IVa, is in general from 0.8 to 3, preferably from 0.95 to 1.5, mol equivalents.

All solvents which do not react themselves with the substrates used are suitable for the reaction. Polar solvents accelerate the reaction. Ethers such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone and dimethylpropyleneurea, or amines such as triethylamine are particularly suitable. The use of mixtures eg. of ethers with amides is often advantageous. Alkyl alcohols and water can also be suitable as mixture components, particularly if the radical B contains a boron atom. The addition of tetraalkylammonium halides or alkali metal halides such as eg. lithium chloride is often helpful and in particular to be recommended if Z is a sulfonyloxy radical. Particularly if the radical B contains a boron atom, it is often useful to add an organic or inorganic base such as potassium carbonate, sodium carbonate, calcium carbonate, calcium hydroxide, sodium hydroxide, potassium hydroxide, potassium phosphate, sodium phosphate, pyridine or an amine such as triethylamine.

The reaction temperature is from -20° to 200° C., preferably from 50° to 160° C. The reaction times are customarily from a few minutes to 50 hours, usually 0.5-10 hours. When using low-boiling solvents, it is sometimes useful to carry out the reaction under autogenous pressure in an autoclave.

If desired, the products of the formula IVb thus obtained can be converted into other intermediates of the formula IVb by further reactons. It may thus be necessary to remove protective groups.

A great variety of peroxides such as hydrogen peroxide, tertbutyl peroxide, organic or inorganic peroxides or their salts such as 3-chloroperbenzoic acid, peracetic acid, performic acid, dibenzoyl peroxide etc. are suitable for the oxidation of IVb to IV. The peroxide can also be prepared in situ from another peroxide, for example peracetic acid from acetic acid and hydrogen peroxide.

The peroxide is preferably employed in the same equivalents as the starting material IVb. An excess can also be used in order to complete the reaction. All solvents are suitable which themselves do not enter into side reactions interfering with the oxidants, such as eg. water, alkyl alcohols, carboxylic acids such as acetic acid or formic acid or halogenated hydrocarbons such as, inter alia, methylene chloride. The reaction temperatures are from -30° C. to 130° C., preferably -10° C. to 80° C.

Aromatic carboxylic acid derivatives of the formula I are obtained, for example, by reacting a corresponding aromatic carboxylic acid derivative of the formula III ##STR8## which is accessible according to the examples mentioned further below, with an appropriate compound of the formula II ##STR9## in the presence of a base.

R²⁰ is chlorine, bromine, iodine, aryl- or alkylsulfonyl such as eg. toluenesulfonyl or methylsulfonyl or another equivalent leaving group. Compounds of the formula II containing a reactive substituent R²⁰ are known in most cases or easy to obtain using common specialist knowledge. Alkali metal or alkaline earth metal hydrides such as NaH or CaH₂, alkali metal hydroxides such as NaOH or KOH, alkali metal alkoxides such as potassium tert-butoxide, alkali metal carbonates such as Na₂ CO₃ or K₂ CO₃, alkali metal amides such as NaNH₂ or lithium diisopropylamide or tertiary amines such as triethylamine or pyridine can be used as base. When using an inorganic base, a phase transfer catalyst can be added if this promotes the conversion. Crown ethers or organic ammonium compounds, for example, are suitable for this.

Many of the customary solvents can be used such as, for example, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, methyl t-butyl ether, diethyl ether, acetone, methyl ethyl ketone, toluene, benzene, dimethoxyethane, dioxane, pyridine or t-butanol. The reaction temperatures are in general from -80° to 150° C., preferably from -10° to 130° C.

If the compounds of the formula I prepared in the manner described are carboxylic acids (ie. if R¹ is hydroxyl), it is also possible to prepare eg. the carboxylic acid derivatives mentioned in claim 2 therefrom by first converting the carboxylic acid into an activated form such as a halide or imidazolide in a customary manner and then reacting this with the appropriate hydroxyl compound of the formula R¹ --H. These two steps can also be simplified, for example, by allowing the carboxylic acid to act on the hydroxyl compound in the presence of a dehydrating agent such as eg. a carbodiimide or a suitable phosphonic anhydride.

Another process for preparing crop protection active compounds of the formula I' starts from intermediates of the formula IV, which are reacted with a salt R¹ M and a heterocycle V: ##STR10## In this case, R², R³, R¹⁴ -R¹⁷, Y, R¹⁸ and R¹⁹ have the meanings described above and the other radicals are:

M an alkali metal cation such as lithium, sodium or potassium, or an equivalent of an alkaline earth metal cation such as magnesium, calcium or barium;

R⁴ halogen such as fluorine, chlorine, bromine, iodine, alkylsulfonyl, particularly methylsulfonyl or haloalkylsulfonyl, particularly trifluoromethylsulfonyl;

R¹ radicals as described above with the exception of hydrogen, the succinylimidoxy group and those radicals OR⁹ in which R⁹ is hydrogen, an alkali metal cation, the equivalent of an alkaline earth metal cation, the ammonium cation or an organic ammonium ion.

The reaction of the intermediates of the formula IV with the salt R¹ M and the further reaction with the heterocycle of the formula V can be carried out in one reaction vessel directly to the active compound I'. In this case, the salt R¹ M, which can also be prepared in situ from a compound R¹ H and a base by well-known processes, is added first. The heterocycle V is then added. V should advantageously only be added if the first step of the reaction, the addition of the salt R¹ M to the intermediate IV, is largely complete. This can last from several minutes to a few hours, the reaction temperature being from -40° C. to 200° C., usually from 0° C. to 130° C.

It is also possible to terminate the reaction after the first stage and to isolate the intermediate III ##STR11## where R is --COR¹. III can then be reacted further by the process described further above.

In both cases the customary solvents are suitable, provided that they cannot be deprotonated themselves by the base or the salt R¹ M used and participate in the reaction. Polar solvents, eg. ethers such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone and dimethylpropyleneurea or dimethyl sulfoxide are particularly highly suitable. A phase transfer catalyst such as a crown ether or a quaternary ammonium salt can be added if this promotes the conversion.

The reaction temperature is from -40° to 200° C., preferably from 0° to 160° C. The reaction times are customarily from a few minutes to 50 hours, usually 0.5-10 hours.

In general, from 0.8 to 3, in particular from 0.9 to 1.5, mol equivalents of the compound R¹ M are employed per mole of starting substance IV. The amount of heterocycle V is likewise expediently from 0.8 to 3, in particular from 0.9 to 1.5, mol equivalents based on IV.

The reaction can be carried out continuously or batchwise at atmospheric pressure, elevated pressure or reduced pressure.

Working-up is carried out in a manner known per se. The possibilities are varied and depend in the individual case on the solubility of the product in the solvents used and on the miscibility of the solvents with water and the boiling points of the solvents. Both aqueous and non-aqueous work-ups are possible. A suitable working-up method consists in mixing the reaction mixture, from which the solvent can also be partially or completely evaporated beforehand, with water and filtering off the product or extracting it with an organic solvent.

The intermediates IVb can also be first reacted by this process as described above to give the compounds VI, which are known in some cases (DE-A-39 19 435) and these can then be converted to the final products as illustrated in the following scheme: ##STR12##

In this case, R is preferably --COR¹, R¹ not being hydrogen, the succinylimidoxy group and those radicals OR⁹ in which R⁹ is hydrogen or one of the cations mentioned.

The reaction conditions for the oxidation correspond to those previously described for the oxidation of IVb to IV. Furthermore, carboxylic acids of the formula I (ie. where R¹ is hydroxyl) can also be reacted as follows to give many of the esters described: to do this the carboxylic acid is first converted into a salt, particularly an alkali metal salt, and this is then made to react, if appropriate in the presence of one of the bases mentioned further above, with an alkylating agent. The alkylating agent has the general formula R¹ -R²¹, the customary leaving groups such as, for example, chlorine, bromine, iodine, aryl- or alkylsulfonyl such as eg. toluenesulfonyl or methylsulfonyl being suitable for R²¹. In general, the alkylating agents are known or they can be prepared in a similar manner to the known compounds.

As herbicides, the compounds I or the compositions containing them and their environmentally tolerable salts eg. of alkali metals and alkaline earth metals can very effectively control broad-leafed weeds and grass weeds in crops such as wheat, rice, maize, soybean and cotton without damaging the crop plants, an effect which occurs especially even at low application rates.

The compounds I or the herbicidal compositions containing them can be applied by spraying, atomizing, dusting, broadcasting or watering, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting compositions, broadcasting compositions or granules. The application forms depend on the intended uses; in each case they should if possible ensure the finest dispersion of the active compounds according to the invention.

The compounds I are generally suitable for preparing directly sprayable solutions, emulsions, pastes or oil dispersions. Suitable inert additives are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, additionally coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone or strongly polar solvents, such as N-methylpyrrolidone or water.

Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by addition of water. To prepare emulsions, pastes or oil dispersions, the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, adhesive, dispersant or emulsifier and possibly solvent or oil can also be prepared, which are suitable for dilution with water.

Suitable surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, eg. lignosulfonic, phenolsulfonic, naphthalenesulfonic and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl-, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol or tributylphenol polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powder, broadcasting and dusting compositions can be prepared by mixing or joint grinding of the active substances with a solid carrier.

Granules, eg. coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.

The formulations in general contain from 0.01 to 95% by weight, preferably from 0.5 to 90% by weight, of active compound. The active compounds are employed here in a purity of from 90% to 100%, preferably from 95% to 100% (by NMR spectrum).

The compounds I according to the invention can be formulated, for example, as follows:

I. 20 parts by weight of the compound No. 2.261 are dissolved in a mixture which consists of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of from 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring out the solution and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02 % by weight of the active compound.

II. 20 parts by weight of the compound No. 2.261 are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.

III. 20 parts by weight of the active compound No. 2.261 are dissolved in a mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210° to 280° C. and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound No. 2.261 are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and the mixture is ground in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray mixture is obtained which contains 0.1% by weight of the active compound.

V. 3 parts by weight of the active compound No. 2.261 are mixed with 97 parts by weight of finely divided kaolin. In this way a dusting composition is obtained which contains 3% by weight of the active compound.

VI. 20 parts by weight of the active compound No. 2.261 are intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

The application of the herbicidal compositions or of the active compounds can be carried out pre-emergence or post-emergence. If the active compounds are less tolerable for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of the spray equipment such that the leaves of the sensitive crop plants are not affected if possible, while the active compounds reach the leaves of undesired plants growing under them or the uncovered soil surface (post-directed, lay-by).

Depending on the target of control, time of year, target plants and stage of growth, the application rates of active compound are from 0.001 to 2.0, preferably from 0.01 to 1.0, kg/ha of active substance (a.s.).

In consideration of the variety of application methods, the compounds I according to the invention or compositions containing them can additionally be employed in a further number of crop plants for the elimination of undesired plants. Suitable crops are, for example, the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

The compounds of the formula I can furthermore affect the various stages of development of a plant and are therefore employed as growth regulators. The varied action of the plant growth regulators is especially dependent on the plant species and variety; on the time of application, relative to the stage of development of the plant, and on the time of year; on the type of application and application process (eg. seed-dressing, soil treatment, foliar application or stem injection in the case of trees); on climatic factors (eg. temperature, amount of precipitation, additionally length of day and light intensity); on the soil condition (including fertilization); on the formulation and application form of the active compound and on the concentrations of the active substance used.

A few of the number of different possibilities for application of the plant growth regulators of the formula I according to the invention in plant cultivation, in agriculture and in horticulture are mentioned below:

A.

The vegetative growth of the plants can be severely inhibited by the compounds which can be used according to the invention, which is manifested in particular in a reduction in the longitudinal growth. The treated plants accordingly exhibit stocky growth; additionally darker leaf coloration is to be observed.

A decreased intensity in the growth of grasses on roadsides, hedgerows, canal banks and on plots of grass such as parks, sports grounds and orchards, ornamental lawns and airfields proves to be advantageous in practice, so that the labor- and cost-intensive mowing can be reduced.

The increase in the resistance of crops susceptible to lodging, such as cereals, maize, sunflowers and soybeans, is also of economic interest. The culm shortening and culm strengthening caused in this case decrease or eliminate the danger of lodging (of being bent over) of plants under unfavorable weather conditions before harvesting.

The application of growth regulators for inhibiting the longitudinal growth and for temporally altering the course of ripening in cotton is also important. Completely mechanized harvesting of this important crop plant is thus made possible.

In the case of fruit and other trees, pruning costs can be saved using the growth regulators. In addition, the alternation of fruit trees can be broken by means of growth regulators.

The lateral branching of the plants can also be increased or inhibited by application of growth regulators. There is interest in this if, eg. in the case of tobacco plants, the formation of side shoots (suckers) is to be inhibited in favor of leaf growth.

In the case of winter rape, for example, the frost resistance can also be considerably increased using growth regulators. In this case, on the one hand, the longitudinal growth and the development of an excessively luxuriant (and thereby particularly frost-susceptible) herbage or biomass are inhibited. On the other hand, after sowing and before the winter frosts set in the young rape plants are held back in the vegetative development stage despite favorable growth conditions. As a result, the frost danger to those plants which are prone to premature degeneration of the inhibition of flowering and to transition into the generative phase is eliminated. Even in other crops, eg. winter cereals, it is advantageous if the populations are indeed well tillered by treatment with compounds according to the invention in the autumn, but are not too luxuriant when going into the winter. As a result, the increased frost sensitivity and, because of the relatively low herbage or biomass, attack by various diseases (eg. fungal disease) can be prevented. The inhibition of the vegetative growth additionally makes possible a more compact planting of the soil with many crop plants, so that an additional yield can be achieved, based on the soil area.

B.

Additional yields both of parts of plants and of plant constituents can be achieved using the growth regulators. Thus it is possible, for example, to induce the growth of greater amounts of buds, flowers, leaves, fruit, seeds, roots and tubers, to increase the content of sugar in sugar beet, sugar cane and citrus fruits, to raise the protein content in cereals or soybeans or to stimulate rubber trees to an increased flow of latex.

In this case, the compounds of the formula I can cause increases in yield by intervention in the plant metabolism or by promotion or inhibition of vegetative and/or of generative growth.

C.

Finally, both reduction or prolongation of the development stages and acceleration or retardation of the ripening of the harvested parts of plants before or after harvesting can be achieved using plant growth regulators.

Of economic interest, for example, is the facilitation of harvesting, which is made possible by the temporally concentrated fall or decrease in the adhesiveness to the tree in the case of citrus fruits, olives or in the case of other species and varieties of pomaceous fruit, stone fruit and hard-shell dry fruit. The same mechanism, that is the promotion of the formation of abscission tissue between the fruit or leaf and shoot part of the plant, is also essential for a well-controllable defoliation of productive plants such as, for example, cotton.

D.

The intensity of irrigation can be reduced by the use of the substances according to the invention and thus a more economical management can be carried out. Under the influence of growth regulators, a better utilization of the water present, for example, occurs because, inter alia, the opening width of the stomata is reduced, a thicker epidermis and cuticle are formed, the root penetration of the soil is improved and the microclimate in the plant population is favorably influenced by a more compact growth.

The compounds I are particularly suitable for culm shortening of crop plants such as barley, rape and wheat.

The growth regulators of the formula I to be used according to the invention can be supplied to the crop plants both from seeds (as seed-dressing agents) and via the soil, ie. by the roots and, particularly preferably, by spraying over the leaf. The compositions are prepared here in a similar manner to the herbicides (see above).

As a result of the high plant compatibility, the application rate of active compound is not critical. The optimum application rate varies depending on the target of control, time of year, target plants and stages of growth.

To widen the spectrum of action and to achieve synergistic effects, the pyridine-N-oxide-substituted salicylic acid derivatives I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, suitable herbicidal mixture components are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiocarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives which carry eg. a carboxyl or carbimino group in the 2-position, quinolinecarboxylic acid derivatives, imidazolines, sulfonamides, sulfonylureas, aryloxy- and heteroaryloxyphenoxypropionic acids and their salts, esters and amides and others. Suitable growth regulators are in particular chlormequat chloride, ethylene and mepiquat chloride.

It may additionally be useful to apply the compounds I on their own or together in combination with other herbicides or growth regulators and additionally mixed with further crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Additionally of interest is the miscibility with mineral salt solutions which are employed for the elimination of nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

SYNTHESIS EXAMPLES Example 1 a) ##STR13## 5-Hydroxy-2,2-dimethyl-4H-(1,3)benzodioxin-4-one

100 g (0.66 mol) of 2,6-dihydroxybenzoic acid are initially introduced into 800 ml of trifluoroacetic acid, and 100 ml of acetone and 216 g (1.98 mol) of trifluoroacetic anhydride are added. The mixture is refluxed for about 2 h, and 50 ml of acetone per hour are then added dropwise under reflux (total reaction time 7.5 h, total acetone addition 375 ml). The reaction mixture is concentrated under reduced pressure at about 55° C., made up three times with toluene and concentrated again, and the residue is finally dried at 45° C. on an oil pump.

The oily product is taken up in 2 l of methyl tert-butyl ether, and the solution is treated with 2 l of water and 2 l of saturated NaHCO₃ solution and stirred for 1.5 h. The aqueous phase is separated off and extracted with methyl tert-butyl ether, and the combined organic phases are washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue is stirred with 200 ml of n-pentane, filtered off with suction and dried. Yield: 115 g (90%). M.p. 60°-62° C.

b) ##STR14## 2,2-Dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

80 g (0.41 mol) of 5-hydroxy-2,2-dimethyl-4H-(1,3)benzodioxin-4-one are dissolved in 1.5 l of methylene chloride, 129 g (1.28 mol) of triethylamine are added at 0° C. and 314 g (1.11 mol) of trifluoromethylsulfonic anhydride are then added dropwise in the course of 2 h. The mixture is allowed to warm to 10° C., is subsequently stirred at this temperature for 10 min and is then added with stirring to 1.5 l of water at 0° C. The organic phase is separated off, the aqueous phase is extracted with methylene chloride, and the combined organic phases are washed with water and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The residue is stirred with 200 ml of n-pentane, filtered off, subsequently washed with n-pentane and dried at 40° C. on an oil pump. Yield: 118 g (88%). Melting point: 115° C.

c) ##STR15## 2,2-Dimethyl-5-(2-methoxypyridin-5-yl)-4H-(1,3)benzodioxin-4-one

8.7 g of 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one, 23.2 g of 2-methoxy-5-tributylstannylpyridine, 3.4 g of lithium chloride, 0.6 g of tetrakistriphenylphosphinepalladium⁰ and 70 mg of 2,6-di-t-butyl-4-methylphenol are dissolved in 150 ml of dioxane and the mixture is stirred for 3 h at 140° C. in an autoclave. It is then concentrated under reduced pressure, the residue is stirred with 200 ml of n-pentane and filtered on a little silica gel 60, the latter is subsequently washed with n-pentane and the product is eluted using ethyl acetate. After concentration, 10.3 g of m.p. 160° C. remain.

d) 2-(4,6-Dimethoxypyrimidin-2-yloxy)-6-(2-methoxypyridin-5-yl)-benzoic acid acetone oxime ester

0.67 g of acetone oxime, dissolved in 30 ml of toluene, is treated with 1.66 g of a 30% strength sodium methoxide solution in methanol and the mixture is concentrated under reduced pressure. 35 ml of dimethylformamide and then 2.50 g of 2,2-dimethyl-5-(2-methoxypyridin-5-yl)-4H-(1,3)benzodioxin-4-one are added, the mixture is stirred for 15 min at room temperature and 1.90 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine are finally added. The reaction mixture is subsequently stirred for several hours, poured into 300 ml of water and extracted with methyl t-butyl ether, and the organic phase is washed thoroughly with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel 60 using n-hexane/ethyl acetate. ¹ H-NMR (CDCl₃): δ=1.65(s); 1.95(s); 3.85(s); 3.98(s); 5.78(s); 6.77(d); 7.3-7.7(m); 8.25(d).

Example 2 a) 2,2-Dimethyl-5-(6-methoxypyridin-2-yl)-4H-(1,3)benzodioxin-4-one

10.9 g of 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)-benzodioxin-4-one, 16.0 g of 6-methoxy-2-tributylstannylpyridine, 4.25 g of lithium chloride, 0.78 g of tetrakistriphenylphosphinepalladium^(O) and 40 mg of 2,6-di-t-butyl-4-methylphenol are dissolved in 120 ml of dioxane and the mixture is stirred for 4 h at 140° C. in an autoclave. It is concentrated under reduced pressure and the product is chromatographed on silica gel 60 using ethyl acetate/toluene. 9.1 g (95%) of a solid of m.p. 130°-132° C. are obtained.

b) Benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)benzoate

1.36 g of benzyl alcohol dissolved in 50 ml of dimethylformamide are treated with 380 mg of sodium hydride (80% strength in liquid paraffin) and the mixture is subsequently stirred at room temperature for about 1 h. 3.0 g of 2,2-dimethyl-5-(6-methoxypyridin-2-yl)-4H-(1,3)benzodioxin-4-one are added, the mixture is stirred at room temperature for 3 h and 2.65 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine are finally added. The mixture is stirred at room temperature for 2 h, at 80° C. for 1.5 h and at 115° C. for 3 h, poured into ice-water containing phosphoric acid and extracted with ethyl acetate, and the organic phase is washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel 60 using cyclohexane/toluene/ethyl acetate. ¹ H-NMR (CDCl₃): δ=3.80(s); 3.89(s); 5.02(s); 5.72(s); 6.67(d=; 6.7-7.7(m)).

Example 3 2,2-Dimethyl-5-(1-oxopyridin-4-yl)-4H-(1,3)benzodioxin-4-one

300 mg of 2,2-dimethyl-5-(pyridin-4-yl)-4H-(1,3)benzodioxin-4-one are initially introduced into 20 ml of methylene chloride, 260 mg of 3-chloroperbenzoic acid are added at room temperature, and the reaction mixture is stirred overnight and worked up directly by chromatography on silica gel 60 using methylene chloride/methanol. Yield: 200 mg. ¹ H-NMR (CDCl₃): δ: 1.80 (s); 6.95 (d); 7.07 (d); 7.25 (d); 7.60 (t); 8.25(d).

Example 4 2,2-Dimethyl-5-(2-methoxy-1-oxopyridin-5-yl)-4H-(1,3)benzodioxin-4-one:

4.17 g of 2,2-dimethyl-5-(2-methoxypyridin-5-yl)-4H-(1,3)benzodioxin-4-one are initially introduced into 200 ml of methylene chloride, 6.0 g of 3-chloroperbenzoic acid are added at room temperature and the reaction mixture is stirred overnight. After addition of some sodium sulfate, the reaction mixture is worked up directly by chromatography on silica gel 60 using methylene chloride/ethyl acetate/methanol. Yield: 2.3 g. M.p.: 82° C.

Example 5 Benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(1-oxopyridin-3-yl)benzoate:

3.0 g of benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(pyridin-3-yl)benzoate are initially introduced into 100 ml of methylene chloride, 2.8 g of 3-chloroperbenzoic acid are added at room temperature, and the reaction mixture is stirred overnight and worked up directly by chromatography on silica gel 60 using methylene chloride/ethyl acetate/methanol. Yield: 3.0 g. ¹ H-NMR (CDCl₃): δ: 3.78 (s); 5.03 (s); 5.73 (s); 7.00-7.40 (m); 7.55 (t); 8.10 (d); 8.27(s).

Example 6 2-(4,6-Dimethoxypyrimidin-2-yloxy)-6-(6-methyl-1-oxopyridin-2-yl)-benzoic acid:

200 mg of 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(6-methylpyridin-2-yl)benzoic acid are initially introduced into 10 ml of acetic acid, 68 mg of 30% strength hydrogen peroxide are added at room temperature, and the reaction mixture is stirred overnight. It is directly concentrated under reduced pressure, the residue is taken up in methylene chloride, and the solution is washed with water, dried over sodium sulfate and again concentrated under reduced pressure. Yield: 190 mg, ¹ H-NMR (d₆ -DMSO): δ: 2.50 (s); 3.82 (s); 5.50 (s); 6.95 (d); 7.02 (d); 7.20-7.35 (m); 7.43 (d); 7.80 (t).

Example 7 2-(4,6-Dimethoxypyrimidin-2-yloxy)-6-(1-oxopyridin-3-yl)-benzoic acid acetone oxime ester:

370 mg of 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(pyridin-3-yl) benzoic acid acetone oxime ester are initially introduced into 25 ml of methylene chloride, 370 mg of 3-chloroperbenzoic acid are added at room temperature, and the reaction mixture is stirred overnight and worked up directly by chromatography on silica gel 60 using methylene chloride/ethyl acetate/methanol. Yield: quantitative. ¹ H-NMR (CDCl₃): δ: 1.74 (s); 1.95 (s); 3.83 (s); 5.77 (s); 7.25-7.45 (m); 7.60 (t); 8.23 (d); 8.34 (s).

Particularly preferred compounds of the formula I which can be prepared as described in the above examples are compiled in the following Tables 1 to 6.

                                      TABLE 1                                      __________________________________________________________________________      ##STR16##                                                                                                                Phys. data                          No.                                                                               R.sup.1    R.sup.3                                                                            X  R.sup.14   R.sup.15                                                                            R.sup.16                                                                          R.sup.17                                                                          .sup.1 H-NMR                        __________________________________________________________________________                                                (DMSO)                              1.001                                                                             OH         OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                      1.002                                                                             OH         OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               H    H  H                                      1.003                                                                             OH         OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               H    H  H                                      1.004                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               H    H  H                                      1.005                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                      1.006                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               H    H  H                                      1.007                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               H    H  H                                      1.008                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               H    H  H                                      1.009                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                      1.010                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               H    H  H                                      1.011                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               H    H  H                                      1.012                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               H    H  H                                      1.013                                                                             OH         OCH.sub.3                                                                          CH 3-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.014                                                                             OH         OCH.sub.3                                                                          CH 4-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.015                                                                             OH         OCH.sub.3                                                                          CH 5-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.016                                                                             OH         OCH.sub.3                                                                          CH 6-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.017                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.018                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.019                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.020                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.021                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.022                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.023                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.024                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-OC.sub.2 H.sub.5                                                                        H    H  H                                      1.025                                                                             OH         OCH.sub.3                                                                          CH 3-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.026                                                                             OH         OCH.sub.3                                                                          CH 4-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.027                                                                             OH         OCH.sub.3                                                                          CH 5-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.028                                                                             OH         OCH.sub.3                                                                          CH 6-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.029                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.030                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.031                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.032                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.033                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.034                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.035                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.036                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-n-C.sub.3 H.sub.7                                                                       H    H  H                                      1.037                                                                             OH         OCH.sub.3                                                                          CH 3-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.038                                                                             OH         OCH.sub.3                                                                          CH 4-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.039                                                                             OH         OCH.sub.3                                                                          CH 5-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.040                                                                             OH         OCH.sub.3                                                                          CH 6-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.041                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.042                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.043                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.044                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.045                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.046                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.047                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.048                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-i-C.sub.3 H.sub.7                                                                       H    H  H                                      1.049                                                                             OH         OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               H    H  H                                      1.050                                                                             OH         OCH.sub.3                                                                          CH 4-SCH.sub.3                                                                               H    H  H                                      1.051                                                                             OH         OCH.sub.3                                                                          CH 5-SCH.sub.3                                                                               H    H  H                                      1.052                                                                             OH         OCH.sub.3                                                                          CH 6-SCH.sub.3                                                                               H    H  H                                      1.053                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               H    H  H                                      1.054                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-SCH.sub.3                                                                               H    H  H                                      1.055                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-SCH.sub.3                                                                               H    H  H                                      1.056                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-SCH.sub.3                                                                               H    H  H                                      1.057                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               H    H  H                                      1.058                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-SCH.sub.3                                                                               H    H  H                                      1.059                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-SCH.sub.3                                                                               H    H  H                                      1.060                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-SCH.sub.3                                                                               H    H  H                                      1.061                                                                             OH         OCH.sub.3                                                                          CH 3-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.062                                                                             OH         OCH.sub.3                                                                          CH 4-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.063                                                                             OH         OCH.sub.3                                                                          CH 5-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.064                                                                             OH         OCH.sub.3                                                                          CH 6-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.065                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.066                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.067                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.068                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.069                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.070                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.071                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-SC.sub.2 H.sub.5                                                                        H    H  H                                      1.072                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-SC.sub.2 H.sub.5                                                                        B    H  H                                      1.073                                                                             OH         OCH.sub.3                                                                          CH 3-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.074                                                                             OH         OCH.sub.3                                                                          CH 4-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.075                                                                             OH         OCH.sub.3                                                                          CH 5-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.076                                                                             OH         OCH.sub.3                                                                          CH 6-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.077                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.078                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.079                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.080                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.081                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.082                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.083                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.084                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                      1.085                                                                             OH         OCH.sub.3                                                                          CH 3-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.086                                                                             OH         OCH.sub.3                                                                          CH 4-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.087                                                                             OH         OCH.sub.3                                                                          CH 5-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.088                                                                             OH         OCH.sub.3                                                                          CH 6-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.089                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.090                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.091                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.092                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.093                                                                             Benzyloxy  OCH.sub.3                                                                          CH 3-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.094                                                                             Benzyloxy  OCH.sub.3                                                                          CH 4-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.095                                                                             Benzyloxy  OCH.sub.3                                                                          CH 5-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.096                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.097                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                      1.098                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                      1.099                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                      1.100                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                      1.101                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                      1.102                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                      1.103                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                    H    H  H                                      1.104                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                    H    H  H                                      1.105                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                    H    H  H                                      1.106                                                                             OH         OCH.sub.3                                                                          CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                      1.107                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                      1.108                                                                             Benzyloxy  OCH.sub.3                                                                          CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                      1.109                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                      1.110                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               H    H  H                                      1.111                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               H    H  H                                      1.112                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               H    H  H                                      1.113                                                                             Propargyloxy                                                                              OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                      1.114                                                                             Propargyloxy                                                                              OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               H    H  H                                      1.115                                                                             Propargyloxy                                                                              OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               H    H  H                                      1.116                                                                             Propargyloxy                                                                              OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               H    H  H                                      1.117                                                                             Allyloxy   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                      1.118                                                                             Allyloxy   OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               H    H  H                                      1.119                                                                             Allyloxy   OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               H    H  H                                      1.120                                                                             Allyloxy   OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               H    H  H                                      1.121                                                                             OH         OCH.sub.2 CH.sub.2                                                                    3-OCH.sub.3                                                                               H    H  H                                      1.122                                                                             OH         OCH.sub.2 CH.sub.2                                                                    4-OCH.sub.3                                                                               H    H  H                                      1.123                                                                             OH         OCH.sub.2 CH.sub.2                                                                    5-OCH.sub.3                                                                               H    H  H                                      1.124                                                                             OH         OCH.sub.2 CH.sub.2                                                                    6-OCH.sub.3                                                                               H    H  H                                      1.125                                                                             OH         OCH.sub.3                                                                          CF 3-OCH.sub.3                                                                               H    H  H                                      1.126                                                                             OH         OCH.sub.3                                                                          CF 4-OCH.sub.3                                                                               H    H  H                                      1.127                                                                             OH         OCH.sub.3                                                                          CF 5-OCH.sub.3                                                                               H    H  H                                      1.128                                                                             OH         OCH.sub.3                                                                          CF 6-OCH.sub.3                                                                               H    H  H                                      1.129                                                                             OH         OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                      1.130                                                                             OH         OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                      1.131                                                                             OH         OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                      1.132                                                                             OH         OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               3-CH.sub.3                                                                          H  H                                      1.133                                                                             OH         OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                      1.134                                                                             OH         OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                      1.135                                                                             OH         OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                      1.136                                                                             OH         OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               3-CH.sub.3                                                                          H  H                                      1.137                                                                             OH         OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                      1.138                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                      1.139                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                      1.140                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               3-CH.sub.3                                                                          H  H                                      1.141                                                                             OH         OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                      1.142                                                                             OH         OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                      1.143                                                                             OH         OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                      1.144                                                                             OH         OCH.sub.3                                                                          CH 4-SCH.sub.3                                                                               3-CH.sub.3                                                                          H  H                                      1.145                                                                             OH         OCH.sub.3                                                                          CH 4-SCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                      1.146                                                                             OH         OCH.sub.3                                                                          CH 4-SCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                      1.147                                                                             OH         OCH.sub.3                                                                          CH 5-SCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                      1.148                                                                             OH         OCH.sub.3                                                                          CH 5-SCH.sub.3                                                                               3-(CH.sub.3)                                                                        H  H                                      1.149                                                                             OH         OCH.sub.3                                                                          CH 5-SCH.sub.3                                                                               6-(CH.sub.3)                                                                        H  H                                      1.150                                                                             OH         OCH.sub.3                                                                          CH 6-SCH.sub.3                                                                               4-(CH.sub.3)                                                                        H  H                                      1.151                                                                             OH         OCH.sub.3                                                                          CH 6-SCH.sub.3                                                                               5-(CH.sub.3)                                                                        H  H                                      1.152                                                                             OH         OCH.sub.3                                                                          CH 6-SCH.sub.3                                                                               3-(CH.sub.3)                                                                        H  H                                      1.153                                                                             OH         OCH.sub.3                                                                          CH 3-Methyl   H    H  H                                      1.154                                                                             OH         OCH.sub.3                                                                          CH 4-Methyl   H    H  H                                      1.155                                                                             OH         OCH.sub.3                                                                          CH 5-Methyl   H    H  H                                      1.156                                                                             OH         OCH.sub.3                                                                          CH 6-Methyl   H    H  H  δ [ppm]: 2.50(s);                                                        3.80(s); 5.50(s);                                                              6.95(d); 7.03(d);                                                              7.30(m); 7.45(d);                                                              7.80(t)                             1.157                                                                             OH         OCH.sub.3                                                                          CH 3-Ethyl    H    H  H                                      1.158                                                                             OH         OCH.sub.3                                                                          CH 4-Ethyl    H    H  H                                      1.159                                                                             OH         OCH.sub.3                                                                          CH 5-Ethyl    H    H  H                                      1.160                                                                             OH         OCH.sub.3                                                                          CH 6-Ethyl    H    H  H                                      1.161                                                                             OH         OCH.sub.3                                                                          CH 3-CF.sub.3 H    H  H                                      1.162                                                                             OH         OCH.sub.3                                                                          CH 4-CF.sub.3 H    H  H                                      1.163                                                                             OH         OCH.sub.3                                                                          CH 5-CF.sub.3 H    H  H                                      1.164                                                                             OH         OCH.sub.3                                                                          CH 6-CF.sub.3 H    H  H                                      1.165                                                                             OH         OCH.sub.3                                                                          CH 3-Cl       H    H  H                                      1.166                                                                             OH         OCH.sub.3                                                                          CH 4-Cl       H    H  H                                      1.167                                                                             OH         OCH.sub.3                                                                          CH 5-Cl       H    H  H                                      1.168                                                                             OH         OCH.sub.3                                                                          CH 6-Cl       H    H  H                                      1.169                                                                             OH         OCH.sub.3                                                                          CH 3-F        H    H  H                                      1.170                                                                             OH         OCH.sub.3                                                                          CH 4-F        H    H  H                                      1.171                                                                             OH         OCH.sub.3                                                                          CH 5-F        H    H  H                                      1.172                                                                             OH         OCH.sub.3                                                                          CH 6-F        H    H  H                                      1.173                                                                             OH         OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.174                                                                             OH         OCH.sub.3                                                                          CH 4-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.175                                                                             OH         OCH.sub.3                                                                          CH 5-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.176                                                                             OH         OCH.sub.3                                                                          CH 6-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.177                                                                             OH         OCH.sub.3                                                                          CH 3-CF.sub.3 6-OCH.sub.3                                                                         H  H                                      1.178                                                                             OH         OCH.sub.3                                                                          CH 4-CF.sub.3 6-OCH.sub.3                                                                         H  H                                      1.179                                                                             OH         OCH.sub.3                                                                          CH 5-CF.sub.3 6-Cl 4-F                                                                               H                                      1.180                                                                             OH         OCH.sub.3                                                                          CH 6-CF.sub.3 4-CH.sub.3                                                                          H  H                                      1.181                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-Methyl   H    H  H                                      1.182                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-Methyl   H    H  H                                      1.183                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-Methyl   H    H  H                                      1.184                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-Methyl   H    H  H                                      1.185                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-Ethyl    H    H  H                                      1.186                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-Ethyl    H    H  H                                      1.187                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-Ethyl    H    H  H                                      1.188                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-Ethyl    H    H  H                                      1.189                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-CF.sub.3 H    H  H                                      1.190                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-CF.sub.3 H    H  H                                      1.191                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-CF.sub.3 H    H  H                                      1.192                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-CF.sub.3 H    H  H                                      1.193                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-Cl       H    H  H                                      1.194                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-Cl       H    H  H                                      1.195                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-Cl       H    H  H                                      1.196                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-Cl       H    H  H                                      1.197                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-F        H    H  H                                      1.198                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-F        H    H  H                                      1.199                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-F        H    H  H                                      1.200                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-F        H    H  H                                      1.201                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.202                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.203                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.204                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.205                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 3-CF.sub.3 6-OCH.sub.3                                                                         H  H                                      1.206                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 4-CF.sub.3 6-OCH.sub.3                                                                         H  H                                      1.207                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 5-CF.sub.3 6-Cl 4-F                                                                               H                                      1.208                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH 6-CF.sub.3 4-CH.sub.3                                                                          H  H                                      1.209                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-Methyl   H    H  H                                      1.210                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-Methyl   H    H  H                                      1.211                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-Methyl   H    H  H                                      1.212                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-Methyl   H    H  H                                      1.213                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-Ethyl    H    H  H                                      1.214                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-Ethyl    H    H  H                                      1.215                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-Ethyl    H    H  H                                      1.216                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-Ethyl    H    H  H                                      1.217                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-CF.sub.3 H    H  H                                      1.218                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-CF.sub.3 H    H  H                                      1.219                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-CF.sub.3 H    H  H                                      1.220                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-CF.sub.3 H    H  H                                      1.221                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-Cl       H    H  H                                      1.222                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-Cl       H    H  H                                      1.223                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-Cl       H    H  H                                      1.224                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-Cl       H    H  H                                      1.225                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-F        H    H  H                                      1.226                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-F        H    H  H                                      1.227                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-F        H    H  H                                      1.228                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-F        H    H  H                                      1.229                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.230                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.231                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                      1.232                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-O-l-C.sub.3 H.sub.7                                                                     H    H  H                                      1.233                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 3-CF.sub.3 6-OCH.sub.3                                                                         H  H                                      1.234                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 4-CF.sub.3 6-OCH.sub.3                                                                         H  H                                      1.235                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 5-CF.sub.3 6-Cl 4-F                                                                               H                                      1.236                                                                             OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                          CH 6-CF.sub.3 4-CH.sub.3                                                                          H  H                                      1.237                                                                             OH         OCH.sub.3                                                                          CH H          H    H  H                                      1.238                                                                             OCH.sub.2 SCH.sub.3                                                                       OCH.sub.3                                                                          CH H          H    H  H                                      1.239                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                                OCH.sub.3                                                                          CH H          H    H  H                                      1.240                                                                             OCH(CH.sub.3)COOC.sub.2 H.sub.5                                                           OCH.sub.3                                                                          CH H          H    H  H                                      1.241                                                                             OCH.sub.2 OCH.sub.3                                                                       OCH.sub.3                                                                          CH H          H    H  H                                      1.242                                                                             Cyclohexaniminoxy                                                                         OCH.sub.3                                                                          CH H          H    H  H                                      1.243                                                                             Cyclopentaniminoxy                                                                        OCH.sub.3                                                                          CH H          H    H  H                                      1.244                                                                             Allyloxy   OCH.sub.3                                                                          CH H          H    H  H                                      1.245                                                                             Propargyloxy                                                                              OCH.sub.3                                                                          CH H          H    H  H                                      1.246                                                                             OH         OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               6-Cl H  H                                      1.247                                                                             OH         OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               6-Cl H  H                                      1.248                                                                             OH         OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               6-Cl H  H                                      1.249                                                                             OH         OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               4-Cl H  H                                      1.250                                                                             OH         OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               4-Cl H  H                                      1.251                                                                             OH         OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               4-Cl H  H                                      1.252                                                                             OH         OCH.sub.3                                                                          CH 3-Methyl   6-Cl H  H                                      1.253                                                                             OH         OCH.sub.3                                                                          CH 4-Methyl   6-Cl H  H                                      1.254                                                                             OH         OCH.sub.3                                                                          CH 5-Methyl   6-Cl H  H                                      1.255                                                                             OH         OCH.sub.3                                                                          CH 3-Methyl   4-Cl H  H                                      1.256                                                                             OH         OCH.sub.3                                                                          CH 6-Methyl   4-Cl H  H                                      1.257                                                                             OH         OCH.sub.3                                                                          CH 5-Methyl   4-Cl H  H                                      1.258                                                                             OH         OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                      1.259                                                                             OH         OCH.sub.3                                                                          CH 4-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                      1.260                                                                             OH         OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                      1.261                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH H          H    H  H                                      __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR17##                                                                                                                    Phys. data                      No.                                                                               R.sup.1    Y R.sup.3                                                                              X  R.sup.14   R.sup.15                                                                            R.sup.16                                                                          R.sup.17                                                                          .sup.1 H-NMR                    __________________________________________________________________________                                                    (CDCl.sub.3)                    2.001                                                                             OH         O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               H    H  H                                  2.002                                                                             OH         O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               H    H  H                                  2.003                                                                             OH         O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               H    H  H                                  2.004                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               H    H  H                                  2.005                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               H    H  H                                  2.006                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               H    H  H                                  2.007                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               H    H  H                                  2.008                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               H    H  H                                  2.009                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               H    H  H                                  2.010                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               H    H  H                                  2.011                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               H    H  H                                  2.012                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               H    H  H                                  2.013                                                                             OH         O OCH.sub.3                                                                            CH 2-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.014                                                                             OH         O OCH.sub.3                                                                            CH 4-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.015                                                                             OH         O OCH.sub.3                                                                            CH 5-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.016                                                                             OH         O OCH.sub.3                                                                            CH 6-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.017                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.018                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.019                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.020                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.021                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.022                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.023                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.024                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-OC.sub.2 H.sub.5                                                                        H    H  H                                  2.025                                                                             OH         O OCH.sub.3                                                                            CH 2-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.026                                                                             OH         O OCH.sub.3                                                                            CH 4-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.027                                                                             OH         O OCH.sub.3                                                                            CH 5-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.028                                                                             OH         O OCH.sub.3                                                                            CH 6-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.029                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.030                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.031                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.032                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.033                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.034                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.035                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.036                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-n-C.sub.3 H.sub.7                                                                       H    H  H                                  2.037                                                                             OH         O OCH.sub.3                                                                            CH 2-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.038                                                                             OH         O OCH.sub.3                                                                            CH 4-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.039                                                                             OH         O OCH.sub.3                                                                            CH 5-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.040                                                                             OH         O OCH.sub.3                                                                            CH 6-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.041                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.042                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.043                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.044                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.045                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.046                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.047                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.048                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-i-C.sub.3 H.sub.7                                                                       H    H  H                                  2.049                                                                             OH         O OCH.sub.3                                                                            CH 2-SCH.sub.3                                                                               H    H  H                                  2.050                                                                             OH         O OCH.sub.3                                                                            CH 4-SCH.sub.3                                                                               H    H  H                                  2.051                                                                             OH         O OCH.sub.3                                                                            CH 5-SCH.sub.3                                                                               H    H  H                                  2.052                                                                             OH         O OCH.sub.3                                                                            CH 6-SCH.sub.3                                                                               H    H  H                                  2.053                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-SCH.sub.3                                                                               H    H  H                                  2.054                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-SCH.sub.3                                                                               H    H  H                                  2.055                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-SCH.sub.3                                                                               H    H  H                                  2.056                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-SCH.sub.3                                                                               H    H  H                                  2.057                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-SCH.sub.3                                                                               H    H  H                                  2.058                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-SCH.sub.3                                                                               H    H  H                                  2.059                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-SCH.sub.3                                                                               H    H  H                                  2.060                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-SCH.sub.3                                                                               H    H  H                                  2.061                                                                             OH         O OCH.sub.3                                                                            CH 2-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.062                                                                             OH         O OCH.sub.3                                                                            CH 4-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.063                                                                             OH         O OCH.sub.3                                                                            CH 5-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.064                                                                             OH         O OCH.sub.3                                                                            CH 6-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.065                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.066                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.067                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.068                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.069                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.070                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.071                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.072                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-SC.sub.2 H.sub.5                                                                        H    H  H                                  2.073                                                                             OH         O OCH.sub.3                                                                            CH 2-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.074                                                                             OH         O OCH.sub.3                                                                            CH 4-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.075                                                                             OH         O OCH.sub.3                                                                            CH 5-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.076                                                                             OH         O OCH.sub.3                                                                            CH 6-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.077                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.078                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.079                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.080                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.081                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.082                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.083                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.084                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-S-n-C.sub.3 H.sub.7                                                                     H    H  H                                  2.085                                                                             OH         O OCH.sub.3                                                                            CH 2-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.086                                                                             OH         O OCH.sub.3                                                                            CH 4-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.087                                                                             OH         O OCH.sub.3                                                                            CH 5-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.088                                                                             OH         O OCH.sub.3                                                                            CH 6-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.089                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.090                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.091                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.092                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.093                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 2-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.094                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 4-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.095                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 5-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.096                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.097                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                  2.098                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                  2.099                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                  2.100                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                  2.101                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                  2.102                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                  2.103                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                         H  H                                  2.104                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                         H  H                                  2.105                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                         H  H                                  2.106                                                                             OH         O OCH.sub.3                                                                            CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                  2.107                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                  2.108                                                                             Benzyloxy  O OCH.sub.3                                                                            CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                  2.109                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               H    H  H                                  2.110                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               H    H  H                                  2.111                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               H    H  H                                  2.112                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               H    H  H                                  2.113                                                                             Propargyloxy                                                                              O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               H    H  H                                  2.114                                                                             Propargyloxy                                                                              O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               H    H  H                                  2.115                                                                             Propargyloxy                                                                              O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               H    H  H                                  2.116                                                                             Propargyloxy                                                                              O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               H    H  H                                  2.117                                                                             Allyloxy   O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               H    H  H                                  2.118                                                                             Allyloxy   O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               H    H  H                                  2.119                                                                             Allyloxy   O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               H    H  H                                  2.120                                                                             Allyloxy   O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               H    H  H                                  2.121                                                                             OH         O OCH.sub.2 CH.sub.2                                                                      2-OCH.sub.3                                                                               H    H  H                                  2.122                                                                             OH         O OCH.sub.2 CH.sub.2                                                                      4-OCH.sub.3                                                                               H    H  H                                  2.123                                                                             OH         O OCH.sub.2 CH.sub.2                                                                      5-OCH.sub.3                                                                               H    H  H                                  2.124                                                                             OH         O OCH.sub.2 CH.sub.2                                                                      6-OCH.sub.3                                                                               H    H  H                                  2.125                                                                             OH         O OCH.sub.3                                                                            CF 2-OCH.sub.3                                                                               H    H  H                                  2.126                                                                             OH         O OCH.sub.3                                                                            CF 4-OCH.sub.3                                                                               H    H  H                                  2.127                                                                             OH         O OCH.sub.3                                                                            CF 5-OCH.sub.3                                                                               H    H  H                                  2.128                                                                             OH         O OCH.sub.3                                                                            CF 6-OCH.sub.3                                                                               H    H  H                                  2.129                                                                             OH         O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                  2.130                                                                             OH         O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  2.131                                                                             OH         O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  2.132                                                                             OH         O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  2.133                                                                             OH         O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  2.134                                                                             OH         O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  2.135                                                                             OH         O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                  2.136                                                                             OH         O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  2.137                                                                             OH         O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  2.138                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                  2.139                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  2.140                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  2.141                                                                             OH         O OCH.sub.3                                                                            CH 2-SCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                  2.142                                                                             OH         O OCH.sub.3                                                                            CH 2-SCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  2.143                                                                             OH         O OCH.sub.3                                                                            CH 2-SCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  2.144                                                                             OH         O OCH.sub.3                                                                            CH 4-SCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  2.145                                                                             OH         O OCH.sub.3                                                                            CH 4-SCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  2.146                                                                             OH         O OCH.sub.3                                                                            CH 4-SCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  2.147                                                                             OH         O OCH.sub.3                                                                            CH 5-SCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                  2.148                                                                             OH         O OCH.sub.3                                                                            CH 5-SCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  2.149                                                                             OH         O OCH.sub.3                                                                            CH 5-SCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  2.150                                                                             OH         O OCH.sub.3                                                                            CH 6-SCH.sub.3                                                                               4-CH.sub.3                                                                          H  H                                  2.151                                                                             OH         O CH.sub.3                                                                             CH 6-SCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  2.152                                                                             OH         O CH.sub.3                                                                             CH 6-SCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  2.153                                                                             OH         O OCH.sub.3                                                                            CH 2-Methyl   H    H  H                                  2.154                                                                             OH         O OCH.sub.3                                                                            CH 4-Methyl   H    H  H                                  2.155                                                                             OH         O OCH.sub.3                                                                            CH 5-Methyl   H    H  H                                  2.156                                                                             OH         O OCH.sub.3                                                                            CH 6-Methyl   H    H  H                                  2.157                                                                             OH         O OCH.sub.3                                                                            CH 2-Ethyl    H    H  H                                  2.158                                                                             OH         O OCH.sub.3                                                                            CH 4-Ethyl    H    H  H                                  2.159                                                                             OH         O OCH.sub.3                                                                            CH 5-Ethyl    H    H  H                                  2.160                                                                             OH         O OCH.sub.3                                                                            CH 6-Ethyl    H    H  H                                  2.161                                                                             OH         O OCH.sub.3                                                                            CH 2-CF.sub.3 H    H  H                                  2.162                                                                             OH         O OCH.sub.3                                                                            CH 4-CF.sub.3 H    H  H                                  2.163                                                                             OH         O OCH.sub.3                                                                            CH 5-CF.sub.3 H    H  H                                  2.164                                                                             OH         O OCH.sub.3                                                                            CH 6-CF.sub.3 H    H  H                                  2.165                                                                             OH         O OCH.sub.3                                                                            CH 2-Cl       H    H  H                                  2.166                                                                             OH         O OCH.sub.3                                                                            CH 4-Cl       H    H  H                                  2.167                                                                             OH         O OCH.sub.3                                                                            CH 5-Cl       H    H  H                                  2.168                                                                             OH         O OCH.sub.3                                                                            CH 6-Cl       H    H  H                                  2.169                                                                             OH         O OCH.sub.3                                                                            CH 2-F        H    H  H                                  2.170                                                                             OH         O OCH.sub.3                                                                            CH 4-F        H    H  H                                  2.171                                                                             OH         O OCH.sub.3                                                                            CH 5-F        H    H  H                                  2.172                                                                             OH         O OCH.sub.3                                                                            CH 6-F        H    H  H                                  2.173                                                                             OH         O OCH.sub.3                                                                            CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.174                                                                             OH         O OCH.sub.3                                                                            CH 4-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.175                                                                             OH         O OCH.sub.3                                                                            CH 5-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.176                                                                             OH         O OCH.sub.3                                                                            CH 6-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.177                                                                             OH         O OCH.sub.3                                                                            CH 2-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  2.178                                                                             OH         O OCH.sub.3                                                                            CH 4-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  2.179                                                                             OH         O OCH.sub.3                                                                            CH 5-CF.sub.3 2-Cl H  H                                  2.180                                                                             OH         O OCH.sub.3                                                                            CH 6-CF.sub.3 2-Cl 4-F                                                                               H                                  2.181                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-Methyl   H    H  H                                  2.182                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-Methyl   H    H  H                                  2.183                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-Methyl   H    H  H                                  2.184                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-Methyl   H    H  H                                  2.185                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-Ethyl    H    H  H                                  2.186                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-Ethyl    H    H  H                                  2.187                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-Ethyl    H    H  H                                  2.188                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-Ethyl    H    H  H                                  2.189                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-CF.sub.3 H    H  H                                  2.190                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-CF.sub.3 H    H  H                                  2.191                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-CF.sub.3 H    H  H                                  2.192                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-CF.sub.3 H    H  H                                  2.193                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-Cl       H    H  H                                  2.194                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-Cl       H    H  H                                  2.195                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-Cl       H    H  H                                  2.196                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-Cl       H    H  H                                  2.197                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-F        H    H  H                                  2.198                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-F        H    H  H                                  2.199                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-F        H    H  H                                  2.200                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-F        H    H  H                                  2.201                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.202                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.203                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.204                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.205                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 2-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  2.206                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 4-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  2.207                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 5-CF.sub.3 2-Cl H  H                                  2.208                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH 6-CF.sub.3 2-Cl 4-F                                                                               H                                  2.209                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-Methyl   H    H  H                                  2.210                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-Methyl   H    H  H                                  2.211                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-Methyl   H    H  H                                  2.212                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-Methyl   H    H  H                                  2.213                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-Ethyl    H    H  H                                  2.214                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-Ethyl    H    H  H                                  2.215                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-Ethyl    H    H  H                                  2.216                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-Ethyl    H    H  H                                  2.217                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-CF.sub.3 H    H  H                                  2.218                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-CF.sub.3 H    H  H                                  2.219                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-CF.sub.3 H    H  H                                  2.220                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-CF.sub.3 H    H  H                                  2.221                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-Cl       H    H  H                                  2.222                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-Cl       H    H  H                                  2.223                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-Cl       H    H  H                                  2.224                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-Cl       H    H  H                                  2.225                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-F        H    H  H                                  2.226                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-F        H    H  H                                  2.227                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-F        H    H  H                                  2.228                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-F        H    H  H                                  2.229                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.230                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.231                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.232                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  2.233                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 2-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  2.234                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 4-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  2.235                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 5-CF.sub.3 2-Cl H  H                                  2.236                                                                             OCH.sub.2 CF.sub.3                                                                        O OCH.sub.3                                                                            CH 6-CF.sub.3 2-Cl 4-F                                                                               H                                  2.237                                                                             OH         O OCH.sub.3                                                                            CH H          H    H  H                                  2.238                                                                             OCH.sub.2 SCH.sub.3                                                                       O OCH.sub.3                                                                            CH H          H    H  H                                  2.239                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                                O OCH.sub.3                                                                            CH H          H    H  H                                  2.240                                                                             OCH(CH.sub.3)COOC.sub.2 H.sub.5                                                           O OCH.sub.3                                                                            CH H          H    H  H                                  2.241                                                                             OCH.sub.2 OCH.sub.3                                                                       O OCH.sub.3                                                                            CH R          H    H  H                                  2.242                                                                             Cyclohexaniminoxy                                                                         O OCH.sub.3                                                                            CH H          H    H  H                                  2.243                                                                             Cyclopentaniminoxy                                                                        O OCH.sub.3                                                                            CH H          H    H  H                                  2.244                                                                             Allyloxy   O OCH.sub.3                                                                            CH H          H    H  H                                  2.245                                                                             Propargyloxy                                                                              O OCH.sub.3                                                                            CH H          H    H  H                                  2.246                                                                             OH         O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               6-Cl H  H                                  2.247                                                                             OH         O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               6-Cl H  H                                  2.248                                                                             OH         O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               6-Cl H  H                                  2.249                                                                             OH         O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               4-Cl H  H                                  2.250                                                                             OH         O OCH.sub.3                                                                            CH 6-OCH.sub.3                                                                               4-Cl H  H                                  2.251                                                                             OH         O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               4-Cl H  H                                  2.252                                                                             OH         O OCH.sub.3                                                                            CH 2-Methyl   6-Cl H  H                                  2.253                                                                             OH         O OCH.sub.3                                                                            CH 4-Methyl   6-Cl H  H                                  2.254                                                                             OH         O OCH.sub.3                                                                            CH 5-Methyl   6-Cl H  H                                  2.255                                                                             OH         O OCH.sub.3                                                                            CH 2-Methyl   4-Cl H  H                                  2.256                                                                             OH         O OCH.sub.3                                                                            CH 6-Methyl   4-Cl H  H                                  2.257                                                                             OH         O OCH.sub.3                                                                            CH 5-Methyl   4-Cl H  H                                  2.258                                                                             OH         O OCH.sub.3                                                                            CH 2-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                  2.259                                                                             OH         O OCH.sub.3                                                                            CH 4-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                  2.260                                                                             OH         O OCH.sub.3                                                                            CH 5-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                  2.261                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            CH H          H    H  H                                  2.262                                                                             2-Propaniminoxy                                                                           O OCH.sub.3                                                                            N  H          H    H  H  δ [ppm]: 1.75(s);                                                        1.95(s); 4.00(s);                                                              7.30(m); 7.62(t);                                                              8.23(m),                        __________________________________________________________________________                                                    8.37(s)                    

                                      TABLE 3                                      __________________________________________________________________________      ##STR18##                                                                     No.                                                                               R.sup.1    Y   R.sup.3                                                                            X  R.sup.14   R.sup.15                                                                            R.sup.16                                                                          R.sup.17                           __________________________________________________________________________     3.001                                                                             OH         O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.002                                                                             OH         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.003                                                                             1-Imidazolyl                                                                              O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.004                                                                             1-Imidazolyl                                                                              O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.005                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.006                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.007                                                                             Methylthiomethyl                                                                          O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.008                                                                             Methylthiomethyl                                                                          O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.009                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.010                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.011                                                                             Cyclohexaniminoxy                                                                         O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.012                                                                             Cyclohexaniminoxy                                                                         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.013                                                                             OH         O   OCH.sub.3                                                                          CH 3-OC.sub.2 H.sub.5                                                                        H    H  H                                  3.014                                                                             OH         O   OCH.sub.3                                                                          CH 2-OC.sub.2 H.sub.5                                                                        H    H  H                                  3.015                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-OC.sub.2 H.sub.5                                                                        H    H  H                                  3.016                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-OC.sub.2 H.sub.5                                                                        H    H  H                                  3.017                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-OC.sub.2 H.sub.5                                                                        H    H  H                                  3.018                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-OC.sub.2 H.sub.5                                                                        H    H  H                                  3.019                                                                             OH         O   OCH.sub.3                                                                          CH 3-n-C.sub.3 H.sub.7                                                                       H    H  H                                  3.020                                                                             OH         O   OCH.sub.3                                                                          CH 2-n-C.sub.3 H.sub.7                                                                       H    H  H                                  3.021                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-n-C.sub.3 H.sub.7                                                                       H    H  H                                  3.022                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-n-C.sub.3 H.sub.7                                                                       H    H  H                                  3.023                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-n-C.sub.3 H.sub.7                                                                       H    H  H                                  3.024                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-n-C.sub.3 H.sub.7                                                                       H    H  H                                  3.025                                                                             OH         O   OCH.sub.3                                                                          CH 3-i-C.sub.3 H.sub.7                                                                       H    H  H                                  3.026                                                                             OH         O   OCH.sub.3                                                                          CH 2-i-C.sub.3 H.sub.7                                                                       H    H  H                                  3.027                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-i-C.sub.3 H.sub.7                                                                       H    H  H                                  3.028                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-i-C.sub.3 H.sub.7                                                                       H    H  H                                  3.029                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-i-C.sub.3 H.sub.7                                                                       H    H  H                                  3.030                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-i-C.sub.3 H.sub.7                                                                       H    H  H                                  3.031                                                                             OH         O   OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               H    H  H                                  3.032                                                                             OH         O   OCH.sub.3                                                                          CH 2-SCH.sub.3                                                                               H    H  H                                  3.033                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               H    H  H                                  3.034                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-SCH.sub.3                                                                               H    H  H                                  3.035                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-SCH.sub.3                                                                               H    H  H                                  3.036                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-SCH.sub.3                                                                               H    H  H                                  3.037                                                                             OH         O   OCH.sub.3                                                                          CH 3-SC.sub.2 H.sub.5                                                                        H    H  H                                  3.038                                                                             OH         O   OCH.sub.3                                                                          CH 2-SC.sub.2 H.sub.5                                                                        H    H  H                                  3.039                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-SC.sub.2 H.sub.5                                                                        H    H  H                                  3.040                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-SC.sub.2 H.sub.5                                                                        H    H  H                                  3.041                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-SC.sub.2 H.sub.5                                                                        H    H  H                                  3.042                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-SC.sub.2 H.sub.5                                                                        H    H  H                                  3.043                                                                             OH         O   OCH.sub.3                                                                          CH 3-O-n-C.sub.3 H.sub.7                                                                     H    H  H                                  3.044                                                                             OH         O   OCH.sub.3                                                                          CH 2-O-n-C.sub.3 H.sub.7                                                                     H    H  H                                  3.045                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-O-n-C.sub.3 H.sub.7                                                                     H    H  H                                  3.046                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-O-n-C.sub.3 H.sub.7                                                                     H    H  H                                  3.047                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-O-n-C.sub.3 H.sub.7                                                                     H    H  H                                  3.048                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-O-n-C.sub.3 H.sub.7                                                                     H    H  H                                  3.049                                                                             OH         O   OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.050                                                                             OH         O   OCH.sub.3                                                                          CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.051                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.052                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.053                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.054                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.055                                                                             OH         O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                  3.056                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                  3.057                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CF.sub.3                                                                      H    H  H                                  3.058                                                                             OH         O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                  3.059                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                  3.060                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    H  H                                  3.061                                                                             OH         O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                    H    H  H                                  3.062                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                    H    H  H                                  3.063                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 6-OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                    H    H  H                                  3.064                                                                             OH         O   OCH.sub.3                                                                          CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                  3.065                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                  3.066                                                                             Benzyloxy  O   OCH.sub.3                                                                          CH 6-ON(CH.sub.3).sub.2                                                                      H    H  H                                  3.067                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.068                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.069                                                                             Propargyloxy                                                                              O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.070                                                                             Propargyloxy                                                                              O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.071                                                                             Allyloxy   O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               H    H  H                                  3.072                                                                             Allyloxy   O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               H    H  H                                  3.073                                                                             OH         O   OCH.sub.2 CH.sub.2                                                                    3-OCH.sub.3                                                                               H    H  H                                  3.074                                                                             OH         O   OCH.sub.2 CH.sub.2                                                                    2-OCH.sub.3                                                                               H    H  H                                  3.075                                                                             OH         O   OCH.sub.3                                                                          CF 3-OCH.sub.3                                                                               H    H  H                                  3.076                                                                             OH         O   OCH.sub.3                                                                          CF 2-OCH.sub.3                                                                               H    H  H                                  3.077                                                                             OH         O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  3.078                                                                             OH         O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  3.079                                                                             OH         O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  3.080                                                                             OH         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               3-CH.sub.3                                                                          H  H                                  3.081                                                                             OH         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  3.082                                                                             OH         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  3.083                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               2-CH.sub.3                                                                          H  H                                  3.084                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  3.085                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  3.086                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               3-CH.sub.3                                                                          H  H                                  3.087                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               5-CH.sub.3                                                                          H  H                                  3.088                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               6-CH.sub.3                                                                          H  H                                  3.089                                                                             OH         O   OCH.sub.3                                                                          CH 2-Methyl   H    H  H                                  3.090                                                                             OH         O   OCH.sub.3                                                                          CH 3-Methyl   H    H  H                                  3.091                                                                             OH         O   OCH.sub.3                                                                          CH 2-Ethyl    H    H  H                                  3.092                                                                             OH         O   OCH.sub.3                                                                          CH 3-Ethyl    H    H  H                                  3.093                                                                             OH         O   OCH.sub.3                                                                          CH 2-CF.sub.3 H    H  H                                  3.094                                                                             OH         O   OCH.sub.3                                                                          CH 3-CF.sub.3 H    H  H                                  3.095                                                                             OH         O   OCH.sub.3                                                                          CH 2-Cl       H    H  H                                  3.096                                                                             OH         O   OCH.sub.3                                                                          CH 3-Cl       H    H  H                                  3.097                                                                             OH         O   OCH.sub.3                                                                          CH 2-F        H    H  H                                  3.098                                                                             OH         O   OCH.sub.3                                                                          CH 3-F        H    H  H                                  3.099                                                                             OH         O   OCH.sub.3                                                                          CH 2-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.100                                                                             OH         O   OCH.sub.3                                                                          CH 3-S-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.101                                                                             OH         O   OCH.sub.3                                                                          CH 2-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  3.102                                                                             OH         O   OCH.sub.3                                                                          CH 3-CF.sub.3 6-OCH.sub.3                                                                         H  H                                  3.103                                                                             OH         O   OCH.sub.3                                                                          CH 5-CF.sub.3 2-Cl H  H                                  3.104                                                                             OH         O   OCH.sub.3                                                                          CH 6-CF.sub.3 2-Cl 4-F                                                                               H                                  3.105                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-Methyl   H    H  H                                  3.106                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-Methyl   H    H  H                                  3.107                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-Ethyl    H    H  H                                  3.108                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-Ethyl    H    H  H                                  3.109                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-CF.sub.3 H    H  H                                  3.110                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-CF.sub.3 H    H  H                                  3.111                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-Cl       H    H  H                                  3.112                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-Cl       H    H  H                                  3.113                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-F        H    H  H                                  3.114                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-F        H    H  H                                  3.115                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.116                                                                             2-Propaniminoxy                                                                           O   OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.117                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 2-Methyl   H    H  H                                  3.118                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 3-Methyl   H    H  H                                  3.119                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 2-Ethyl    H    H  H                                  3.120                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 3-Ethyl    H    H  H                                  3.121                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 2-CF.sub.3 H    H  H                                  3.122                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 3-CF.sub.3 H    H  H                                  3.123                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 3-Cl       H    H  H                                  3.124                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 2-Cl       H    H  H                                  3.125                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 2-F        H    H  H                                  3.126                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 3-F        H    H  H                                  3.127                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 2-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.128                                                                             OCH.sub.2 CF.sub.3                                                                        O   OCH.sub.3                                                                          CH 3-O-i-C.sub.3 H.sub.7                                                                     H    H  H                                  3.129                                                                             OH         O   OCH.sub.3                                                                          CH H          H    H  H                                  3.130                                                                             OCH.sub.2 SCH.sub.3                                                                       O   OCH.sub.3                                                                          CH H          H    H  H                                  3.131                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                                O   OCH.sub.3                                                                          CH H          H    H  H                                  3.132                                                                             OCH(CH.sub.3)COOC.sub.2 H.sub.5                                                           O   OCH.sub.3                                                                          CH H          H    H  H                                  3.133                                                                             OCH.sub.2 OCH.sub.3                                                                       O   OCH.sub.3                                                                          CH H          H    H  H                                  3.134                                                                             Cyclohexaniminoxy                                                                         O   OCH.sub.3                                                                          CH H          H    H  H                                  3.135                                                                             Cyclopentaniminoxy                                                                        O   OCH.sub.3                                                                          CH H          H    H  H                                  3.136                                                                             Allyloxy   O   OCH.sub.3                                                                          CH H          H    H  H                                  3.137                                                                             Propargyloxy                                                                              O   OCH.sub.3                                                                          CH H          H    H  H                                  3.138                                                                             OH         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               6-Cl H  H                                  3.139                                                                             OH         O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               6-Cl H  H                                  3.140                                                                             OH         O   OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               6-Cl H  H                                  3.141                                                                             OH         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               3-Cl H  H                                  3.142                                                                             OH         O   OCH.sub.3                                                                          CH 6-OCH.sub.3                                                                               3-Cl H  H                                  3.143                                                                             OH         O   OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               3-Cl H  H                                  3.144                                                                             OH         O   OCH.sub.3                                                                          CH 2-Methyl   6-Cl H  H                                  3.145                                                                             OH         O   OCH.sub.3                                                                          CH 3-Methyl   6-Cl H  H                                  3.146                                                                             OH         O   OCH.sub.3                                                                          CH 5-Methyl   6-Cl H  H                                  3.147                                                                             OH         O   OCH.sub.3                                                                          CH 2-Methyl   3-Cl H  H                                  3.148                                                                             OH         O   OCH.sub.3                                                                          CH 6-Methyl   3-Cl H  H                                  3.149                                                                             OH         O   OCH.sub.3                                                                          CH 5-Methyl   3-Cl H  H                                  3.150                                                                             OH         O   OCH.sub.3                                                                          CH 2-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                  3.151                                                                             OH         O   OCH.sub.3                                                                          CH 3-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                  3.152                                                                             OH         O   OCH.sub.3                                                                          CH 5-OCH.sub.3                                                                               6-OCH.sub.3                                                                         H  H                                  3.153                                                                             2-Propaniminoxy                                                                           OCH.sub.3                                                                          CH  H  H          H                                          __________________________________________________________________________

                  TABLE 4                                                          ______________________________________                                          ##STR19##                                                                     ______________________________________                                    

Compounds of the abovementioned formula, in which the combination of the substituents R¹, R³, X and R¹⁴ -R¹⁷ for one compound in each case corresponds to one line of Table 1. Table 4 therefore relates to compounds having the numbers 4.001 to 4.261, No. 4.001 corresponding to No. 1.001 from Table 1, but with Y═S instead of O.

                  TABLE 5                                                          ______________________________________                                          ##STR20##                                                                     ______________________________________                                    

Compounds of the abovementioned formula, in which the combination of the substituents R¹, R³, X and R¹⁴ -R¹⁷ for one compound in each case corresponds to one line of Table 2. Table 5 therefore relates to compounds having the numbers 5.001 to 5.261, No. 5.001 corresponding to No. 2.001 from Table 2, but with Y═S instead of O.

                  TABLE 6                                                          ______________________________________                                          ##STR21##                                                                     ______________________________________                                    

Compounds of the abovementioned formula, in which the combination of the substituents R¹, R³, X and R¹⁴ -R¹⁷ for one compound in each case corresponds to one line of Table 3. Table 6 therefore relates to compounds having the numbers 6.001 to 6.153, No. 6.001 corresponding to No. 3.001 from Table 3, but with Y═S instead of O.

Intermediates of the formula IV are compiled in the following Table 7.

                                      TABLE 7                                      __________________________________________________________________________      ##STR22##                            IV                                       No.                                                                               Py                    R.sup.18                                                                           R.sup.19                                                                          Y phys. data                                   __________________________________________________________________________     7.001                                                                             1-Oxopyridin-2-yl     CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.002                                                                             1-Oxopyridin-2-yl     CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.003                                                                             1-Oxopyridin-3-yl     CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.004                                                                             1-Oxopyridin-3-yl     CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.005                                                                             1-Oxopyridin-4-yl     CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.006                                                                             1-Oxopyridin-4-yl     CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.007                                                                             3-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.008                                                                             3-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.009                                                                             4-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.010                                                                             4-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.011                                                                             5-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.012                                                                             5-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.013                                                                             6-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.014                                                                             6-Methoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.015                                                                             2-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.016                                                                             2-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.017                                                                             4-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.018                                                                             4-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.019                                                                             5-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.020                                                                             5-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.021                                                                             6-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.022                                                                             6-Methoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.023                                                                             2-Methoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.024                                                                             2-Methoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.025                                                                             3-Methoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.026                                                                             3-Methoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.027                                                                             3-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.028                                                                             3-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.029                                                                             4-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.030                                                                             4-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.031                                                                             5-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.032                                                                             5-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.033                                                                             6-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.034                                                                             6-Ethoxy-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.035                                                                             2-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.036                                                                             2-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.037                                                                             4-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.038                                                                             4-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.039                                                                             5-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.040                                                                             5-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.041                                                                             6-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.042                                                                             6-Ethoxy-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.043                                                                             2-Ethoxy-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.044                                                                             2-Ethoxy-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.045                                                                             3-Ethoxy-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.046                                                                             3-Ethoxy-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.047                                                                             3-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.048                                                                             3-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.049                                                                             4-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.050                                                                             4-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.051                                                                             5-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.052                                                                             5-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.053                                                                             6-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.054                                                                             6-Isopropoxy-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.055                                                                             2-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.056                                                                             2-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.057                                                                             4-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.058                                                                             4-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.059                                                                             5-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.060                                                                             5-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.061                                                                             6-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.062                                                                             6-Isopropoxy-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.063                                                                             2-Isopropoxy-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.064                                                                             2-Isopropoxy-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.065                                                                             3-Isopropoxy-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.066                                                                             3-Isopropoxy-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.067                                                                             3-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.068                                                                             3-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.069                                                                             4-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.070                                                                             4-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.071                                                                             5-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.072                                                                             5-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.073                                                                             6-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.074                                                                             6-Methylthio-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.075                                                                             2-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.076                                                                             2-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.077                                                                             4-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.078                                                                             4-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.079                                                                             5-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.080                                                                             5-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.081                                                                             6-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.082                                                                             6-Methylthio-1-oxopyridin-3-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.083                                                                             2-Methylthio-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.084                                                                             2-Methylthio-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.085                                                                             3-Methylthio-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.086                                                                             3-Methylthio-1-oxopyridin-4-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.087                                                                             3-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.088                                                                             3-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.089                                                                             4-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.090                                                                             4-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.091                                                                             5-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.092                                                                             5-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.093                                                                             6-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.094                                                                             6-Propoxy-1-oxopyridin-2-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.095                                                                             2-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.096                                                                             2-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.097                                                                             4-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.098                                                                             4-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.099                                                                             5-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.100                                                                             5-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.101                                                                             6-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.102                                                                             6-Propoxy-1-oxopyridin-3-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.103                                                                             2-Propoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.104                                                                             2-Propoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.105                                                                             3-Propoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.106                                                                             3-Propoxy-1-oxopyridin-4-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.107                                                                             3-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.108                                                                             3-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.109                                                                             4-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.110                                                                             4-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.111                                                                             5-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.112                                                                             5-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.113                                                                             6-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.114                                                                             6-Trifluoromethyl-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.115                                                                             2-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.116                                                                             2-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.117                                                                             4-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.118                                                                             4-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.119                                                                             5-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.120                                                                             5-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.121                                                                             6-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.122                                                                             6-Trifluoromethyl-1-oxopyridin-3-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.123                                                                             2-Trifluoromethyl-1-oxopyridin-4-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.124                                                                             2-Trifluoromethyl-1-oxopyridin-4-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.125                                                                             3-Trifluoromethyl-1-oxopyridin-4-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.126                                                                             3-Trifluoromethyl-1-oxopyridin-4-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.127                                                                             3-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.128                                                                             3-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.129                                                                             4-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.130                                                                             4-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.131                                                                             5-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.132                                                                             5-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.133                                                                             6-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.134                                                                             6-Fluoro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.135                                                                             2-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.136                                                                             2-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.137                                                                             4-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.138                                                                             4-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.139                                                                             5-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.140                                                                             5-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.141                                                                             6-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.142                                                                             6-Fluoro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.143                                                                             2-Fluoro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.144                                                                             2-Fluoro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.145                                                                             3-Fluoro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.146                                                                             3-Fluoro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.147                                                                             3-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.148                                                                             3-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.149                                                                             4-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.150                                                                             4-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.151                                                                             5-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.152                                                                             5-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.153                                                                             6-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.154                                                                             6-Chloro-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.155                                                                             2-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.156                                                                             2-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.157                                                                             4-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.158                                                                             4-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.159                                                                             5-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.160                                                                             5-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.161                                                                             6-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.162                                                                             6-Chloro-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.163                                                                             2-Chloro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.164                                                                             2-Chloro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.165                                                                             3-Chloro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.166                                                                             3-Chloro-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.167                                                                             3-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.168                                                                             3-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.169                                                                             4-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.170                                                                             4-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.171                                                                             5-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.172                                                                             5-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.173                                                                             6-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.174                                                                             6-Methyl-1-oxopyridin-2-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.175                                                                             2-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.176                                                                             2-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.177                                                                             4-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.178                                                                             4-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.179                                                                             5-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.180                                                                             5-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.181                                                                             6-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.182                                                                             6-Methyl-1-oxopyridin-3-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.183                                                                             2-Methyl-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.184                                                                             2-Methyl-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.185                                                                             3-Methyl-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.186                                                                             3-Methyl-1-oxopyridin-4-yl                                                                           CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.187                                                                             3-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.188                                                                             3-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.189                                                                             4-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.190                                                                             4-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.191                                                                             5-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.192                                                                             5-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.193                                                                             6-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.194                                                                             6-Ethyl-1-oxopyridin-2-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.195                                                                             2-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.196                                                                             2-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.197                                                                             4-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.198                                                                             4-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.199                                                                             5-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.200                                                                             5-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.201                                                                             6-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.202                                                                             6-Ethyl-1-oxopyridin-3-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.203                                                                             2-Ethyl-1-oxopyridin-4-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.204                                                                             2-Ethyl-1-oxopyridin-4-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.205                                                                             3-Ethyl-1-oxopyridin-4-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.206                                                                             3-Ethyl-1-oxopyridin-4-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.207                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.208                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.209                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.210                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.211                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.212                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.213                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.214                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.215                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.216                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.217                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.218                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.219                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.220                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.221                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.222                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.223                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.224                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.225                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.226                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.227                                                                             3,5-Dimethyl-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.228                                                                             3,5-Dimethyl-1-oxopyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.229                                                                             6-Methoxy-4-methyl-1-oxopyridin-2-yl                                                                 CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.230                                                                             6-Methoxy-4-methyl-1-oxopyridin-2-yl                                                                 CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.231                                                                             5-(2,2,2-Trifluoroethoxy)-1-oxopyridin-2-yl                                                          CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.232                                                                             5-(2,2,2-Trifluoroethoxy)-1-oxopyridin-2-yl                                                          CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.233                                                                             6-Dimethylamino-1-oxopyridin-2-yl                                                                    CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.234                                                                             6-Dimethylamino-1-oxopyridin-2-yl                                                                    CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.235                                                                             2-Methoxy-5-trifluoromethyl-1-oxopyridin-3-yl                                                        CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.236                                                                             2-Methoxy-5-trifluoromethyl-1-oxopyridin-3-yl                                                        CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.237                                                                             6-Dimethylaminoxy-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.238                                                                             6-Dimethylaminoxy-1-oxopyridin-2-yl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.239                                                                             6-Isopropyl-1-oxopyridin-2-yl                                                                        CH.sub.3                                                                           CH.sub.3                                                                          O                                              7.240                                                                             6-Isopropyl-1-oxopyridin-4-yl                                                                        CH.sub.3                                                                           CH.sub.3                                                                          S                                              7.241                                                                             1-Oxopyridin-2-yl     C.sub.6 H.sub.5                                                                    H  O                                              7.242                                                                             1-Oxopyridin-2-yl     t-C.sub.4 H.sub.9                                                                  H  O                                              7.243                                                                             1-Oxopyridin-4-yl     C.sub.6 H.sub.5                                                                    CH.sub.3                                                                          O                                              7.244                                                                             1-Oxopyridin-4-yl     C.sub.2 H.sub.5                                                                    CH.sub.3                                                                          S                                              __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________      ##STR23##                             III                                     No.                                                                               Py                    R.sup.1  Y phys. data                                 __________________________________________________________________________     8.001                                                                             1-Oxopyridin-2-yl     2-Propaniminoxy                                                                         O                                            8.002                                                                             1-Oxopyridin-2-yl     2-Propaniminoxy                                                                         S                                            8.003                                                                             1-Oxopyridin-3-yl     2-Propaniminoxy                                                                         O                                            8.004                                                                             1-Oxopyridin-3-yl     2-Propaniminoxy                                                                         S                                            8.005                                                                             1-Oxopyridin-4-yl     2-Propaniminoxy                                                                         O                                            8.006                                                                             1-Oxopyridin-4-yl     2-Propaniminoxy                                                                         S                                            8.007                                                                             3-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.008                                                                             3-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.009                                                                             4-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.010                                                                             4-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.011                                                                             5-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.012                                                                             5-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.013                                                                             6-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.014                                                                             6-Methoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.015                                                                             2-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.016                                                                             2-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.017                                                                             4-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.018                                                                             4-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.019                                                                             5-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.020                                                                             5-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.021                                                                             6-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.022                                                                             6-Methoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.023                                                                             2-Methoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         O                                            8.024                                                                             2-Methoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         S                                            8.025                                                                             3-Methoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         O                                            8.026                                                                             3-Methoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         S                                            8.027                                                                             3-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.028                                                                             3-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.029                                                                             4-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.030                                                                             4-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.031                                                                             5-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.032                                                                             5-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.033                                                                             6-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.034                                                                             6-Ethoxy-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.035                                                                             2-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.036                                                                             2-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.037                                                                             4-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.038                                                                             4-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.039                                                                             5-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.040                                                                             5-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.041                                                                             6-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.042                                                                             6-Ethoxy-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.043                                                                             2-Ethoxy-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.044                                                                             2-Ethoxy-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.045                                                                             3-Ethoxy-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.046                                                                             3-Ethoxy-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.047                                                                             3-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.048                                                                             3-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.049                                                                             4-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.050                                                                             4-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.051                                                                             5-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.052                                                                             5-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.053                                                                             6-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.054                                                                             6-Isopropoxy-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.055                                                                             2-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.056                                                                             2-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.057                                                                             4-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.058                                                                             4-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.059                                                                             5-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.060                                                                             5-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.061                                                                             6-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.062                                                                             6-Isopropoxy-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.063                                                                             2-Isopropoxy-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         O                                            8.064                                                                             2-Isopropoxy-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         S                                            8.065                                                                             3-Isopropoxy-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         O                                            8.066                                                                             3-Isopropoxy-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         S                                            8.067                                                                             3-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.068                                                                             3-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.069                                                                             4-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.070                                                                             4-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.071                                                                             5-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.072                                                                             5-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.073                                                                             6-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.074                                                                             6-Methylthio-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.075                                                                             2-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.076                                                                             2-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.077                                                                             4-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.078                                                                             4-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.079                                                                             5-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.080                                                                             5-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.081                                                                             6-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         O                                            8.082                                                                             6-Methylthio-1-oxopyridin-3-yl                                                                       2-Propaniminoxy                                                                         S                                            8.083                                                                             2-Methylthio-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         O                                            8.084                                                                             2-Methylthio-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         S                                            8.085                                                                             3-Methylthio-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         O                                            8.086                                                                             3-Methylthio-1-oxopyridin-4-yl                                                                       2-Propaniminoxy                                                                         S                                            8.087                                                                             3-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.088                                                                             3-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.089                                                                             4-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.090                                                                             4-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.091                                                                             5-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.092                                                                             5-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.093                                                                             6-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         O                                            8.094                                                                             6-Propoxy-1-oxopyridin-2-yl                                                                          2-Propaniminoxy                                                                         S                                            8.095                                                                             2-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.096                                                                             2-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.097                                                                             4-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.098                                                                             4-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.099                                                                             5-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.100                                                                             5-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.101                                                                             6-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         O                                            8.102                                                                             6-Propoxy-1-oxopyridin-3-yl                                                                          2-Propaniminoxy                                                                         S                                            8.103                                                                             2-Propoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         O                                            8.104                                                                             2-Propoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         S                                            8.105                                                                             3-Propoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         O                                            8.106                                                                             3-Propoxy-1-oxopyridin-4-yl                                                                          2-Propaniminoxy                                                                         S                                            8.107                                                                             3-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         O                                            8.108                                                                             3-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         S                                            8.109                                                                             4-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         O                                            8.110                                                                             4-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         S                                            8.111                                                                             5-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         O                                            8.112                                                                             5-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         S                                            8.113                                                                             6-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         O                                            8.114                                                                             6-Trifluoromethyl-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         S                                            8.115                                                                             2-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         O                                            8.116                                                                             2-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         S                                            8.117                                                                             4-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         O                                            8.118                                                                             4-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         S                                            8.119                                                                             5-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         O                                            8.120                                                                             5-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         S                                            8.121                                                                             6-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         O                                            8.122                                                                             6-Trifluoromethyl-1-oxopyridin-3-yl                                                                  2-Propaniminoxy                                                                         S                                            8.123                                                                             2-Trifluoromethyl-1-oxopyridin-4-yl                                                                  2-Propaniminoxy                                                                         O                                            8.124                                                                             2-Trifluoromethyl-1-oxopyridin-4-yl                                                                  2-Propaniminoxy                                                                         S                                            8.125                                                                             3-Trifluoromethyl-1-oxopyridin-4-yl                                                                  2-Propaniminoxy                                                                         O                                            8.126                                                                             3-Trifluoromethyl-1-oxopyridin-4-yl                                                                  2-Propaniminoxy                                                                         S                                            8.127                                                                             3-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.128                                                                             3-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.129                                                                             4-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.130                                                                             4-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.131                                                                             5-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.132                                                                             5-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.133                                                                             6-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.134                                                                             6-Fluoro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.135                                                                             2-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.136                                                                             2-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.137                                                                             4-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.138                                                                             4-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.139                                                                             5-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.140                                                                             5-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.141                                                                             6-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.142                                                                             6-Fluoro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.143                                                                             2-Fluoro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.144                                                                             2-Fluoro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.145                                                                             3-Fluoro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.146                                                                             3-Fluoro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.147                                                                             3-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.148                                                                             3-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.149                                                                             4-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.150                                                                             4-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.151                                                                             5-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.152                                                                             5-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.153                                                                             6-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.154                                                                             6-Chloro-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.155                                                                             2-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.156                                                                             2-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.157                                                                             4-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.158                                                                             4-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.159                                                                             5-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.160                                                                             5-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.161                                                                             6-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.162                                                                             6-Chloro-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.163                                                                             2-Chloro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.164                                                                             2-Chloro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.165                                                                             3-Chloro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.166                                                                             3-Chloro-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.167                                                                             3-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.168                                                                             3-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.169                                                                             4-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.170                                                                             4-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.171                                                                             5-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.172                                                                             5-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.173                                                                             6-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         O                                            8.174                                                                             6-Methyl-1-oxopyridin-2-yl                                                                           2-Propaniminoxy                                                                         S                                            8.175                                                                             2-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.176                                                                             2-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.177                                                                             4-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.178                                                                             4-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.179                                                                             5-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.180                                                                             5-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.181                                                                             6-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         O                                            8.182                                                                             6-Methyl-1-oxopyridin-3-yl                                                                           2-Propaniminoxy                                                                         S                                            8.183                                                                             2-Methyl-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.184                                                                             2-Methyl-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.185                                                                             3-Methyl-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         O                                            8.186                                                                             3-Methyl-1-oxopyridin-4-yl                                                                           2-Propaniminoxy                                                                         S                                            8.187                                                                             3-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         O                                            8.188                                                                             3-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         S                                            8.189                                                                             4-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         O                                            8.190                                                                             4-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         S                                            8.191                                                                             5-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         O                                            8.192                                                                             5-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         S                                            8.193                                                                             6-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         O                                            8.194                                                                             6-Ethyl-1-oxopyridin-2-yl                                                                            2-Propaniminoxy                                                                         S                                            8.195                                                                             2-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         O                                            8.196                                                                             2-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         S                                            8.197                                                                             4-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         O                                            8.198                                                                             4-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         S                                            8.199                                                                             5-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         O                                            8.200                                                                             5-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         S                                            8.201                                                                             6-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         O                                            8.202                                                                             6-Ethyl-1-oxopyridin-3-yl                                                                            2-Propaniminoxy                                                                         S                                            8.203                                                                             2-Ethyl-1-oxopyridin-4-yl                                                                            2-Propaniminoxy                                                                         O                                            8.204                                                                             2-Ethyl-1-oxopyridin-4-yl                                                                            2-Propaniminoxy                                                                         S                                            8.205                                                                             3-Ethyl-1-oxopyridin-4-yl                                                                            2-Propaniminoxy                                                                         O                                            8.206                                                                             3-Ethyl-1-oxopyridin-4-yl                                                                            2-Propaniminoxy                                                                         S                                            8.207                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         O                                            8.208                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         S                                            8.209                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         O                                            8.210                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         S                                            8.211                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         O                                            8.212                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         S                                            8.213                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         O                                            8.214                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-2-yl                                                                2-Propaniminoxy                                                                         S                                            8.215                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         O                                            8.216                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         S                                            8.217                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         O                                            8.218                                                                             4-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         S                                            8.219                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         O                                            8.220                                                                             5-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         S                                            8.221                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         O                                            8.222                                                                             6-(2-Methoxyethoxy)-1-oxopyridin-3-yl                                                                2-Propaniminoxy                                                                         S                                            8.223                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                2-Propaniminoxy                                                                         O                                            8.224                                                                             2-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                2-Propaniminoxy                                                                         S                                            8.225                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                2-Propaniminoxy                                                                         O                                            8.226                                                                             3-(2-Methoxyethoxy)-1-oxopyridin-4-yl                                                                2-Propaniminoxy                                                                         S                                            8.227                                                                             3,5-Dimethyl-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         O                                            8.228                                                                             3,5-Dimethyl-1-oxopyridin-2-yl                                                                       2-Propaniminoxy                                                                         S                                            8.229                                                                             6-Methoxy-4-methyl-1-oxopyridin-2-yl                                                                 2-Propaniminoxy                                                                         O                                            8.230                                                                             6-Methoxy-4-methyl-1-oxopyridin-2-yl                                                                 2-Propaniminoxy                                                                         S                                            8.231                                                                             5-(2,2,2-Trifluoroethoxy)-1-oxopyridin-2-yl                                                          2-Propaniminoxy                                                                         O                                            8.232                                                                             5-(2,2,2-Trifluoroethoxy)-1-oxopyridin-2-yl                                                          2-Propaniminoxy                                                                         S                                            8.233                                                                             6-Dimethylamino-1-oxopyridin-2-yl                                                                    2-Propaniminoxy                                                                         O                                            8.234                                                                             6-Dimethylamino-1-oxopyridin-2-yl                                                                    2-Propaniminoxy                                                                         S                                            8.235                                                                             2-Methoxy-5-trifluoromethyl-1-oxopyridin-3-yl                                                        2-Propaniminoxy                                                                         O                                            8.236                                                                             2-Methoxy-5-trifluoromethyl-1-oxopyridin-3-yl                                                        2-Propaniminoxy                                                                         S                                            8.237                                                                             6-Dimethylaminoxy-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         O                                            8.238                                                                             6-Dimethylaminoxy-1-oxopyridin-2-yl                                                                  2-Propaniminoxy                                                                         S                                            8.239                                                                             6-Isopropyl-1-oxopyridin-2-yl                                                                        2-Propaniminoxy                                                                         O                                            8.240                                                                             6-Isopropyl-1-oxopyridin-4-yl                                                                        2-Propaniminoxy                                                                         S                                            8.241                                                                             1-Oxopyridin-2-yl     Benzyloxy                                                                               O                                            8.242                                                                             1-Oxopyridin-2-yl     Benzyloxy                                                                               S                                            8.243                                                                             1-Oxopyridin-3-yl     Benzyloxy                                                                               O                                            8.244                                                                             1-Oxopyridin-3-yl     Benzyloxy                                                                               S                                            8.245                                                                             1-Oxopyridin-4-yl     Benzyloxy                                                                               O                                            8.246                                                                             1-Oxopyridin-4-yl     Benzyloxy                                                                               S                                            8.247                                                                             1-Oxopyridin-2-yl     Methoxy  O                                            8.248                                                                             1-Oxopyridin-2-yl     Methoxy  S                                            8.249                                                                             1-Oxopyridin-3-yl     Methoxy  O                                            8.259                                                                             1-Oxopyridin-3-yl     Methoxy  S                                            8.260                                                                             1-Oxopyridin-4-yl     Methoxy  O                                            8.261                                                                             1-Oxopyridin-4-yl     Methoxy  S                                            8.262                                                                             1-Oxopyridin-2-yl     Hydroxyl O                                            8.263                                                                             1-Oxopyridin-2-yl     Hydroxyl S                                            8.264                                                                             1-Oxopyridin-3-yl     Hydroxyl O                                            8.265                                                                             1-Oxopyridin-3-yl     Hydroxyl S                                            8.266                                                                             1-Oxopyridin-4-yl     Hydroxyl O                                            8.267                                                                             1-Oxopyridin-4-yl     Hydroxyl S                                            8.268                                                                             1-Oxopyridin-2-yl     Propargyloxy                                                                            O                                            8.269                                                                             1-Oxopyridin-2-yl     Propargyloxy                                                                            S                                            8.270                                                                             1-Oxopyridin-3-yl     Propargyloxy                                                                            O                                            8.271                                                                             1-Oxopyridin-3-yl     Propargyloxy                                                                            S                                            8.272                                                                             1-Oxopyridin-4-yl     Propargyloxy                                                                            O                                            8.273                                                                             1-Oxopyridin-4-yl     Propargyloxy                                                                            S                                            8.274                                                                             1-Oxopyridin-2-yl     OCH.sub.2 CF.sub.3                                                                      O                                            8.275                                                                             1-Oxopyridin-2-yl     OCH.sub.2 CF.sub.3                                                                      S                                            8.276                                                                             1-Oxopyridin-3-yl     OCH.sub.2 CF.sub.3                                                                      O                                            8.277                                                                             1-Oxopyridin-3-yl     OCH.sub.2 CF.sub.3                                                                      S                                            8.278                                                                             1-Oxopyridin-4-yl     OCH.sub.2 CF.sub.3                                                                      O                                            8.279                                                                             1-Oxopyridin-4-yl     OCH.sub.2 CF.sub.3                                                                      S                                            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Use Examples

It was possible to show the herbicidal and growth-regulatory action of the compounds of the formula I by greenhouse tests:

The cultivation containers used were plastic pots containing loamy sand with about 3.0% humus as a substrate. The seeds of the test plants were sown separately according to species.

In the case of pre-emergence treatment, the active compounds suspended or emulsified in water were applied directly after sowing by means of finely dispersing nozzles. The containers were lightly watered in order to promote germination and growth and then covered with transparent plastic hoods until the plants had taken root. This covering causes a uniform germination of the test plants if this has not been adversely affected by the active compounds.

For the purpose of post-emergence treatment, the test plants, depending on growth form, were first raised to a growth height of from 3 to 15 cm and only then treated with the active compounds suspended or emulsified in water. To do this, the test plants were either sown directly and raised in the same containers or they were first raised separately as seed plants and transplanted into the test containers a few days before the treatment.

The plants were kept in a species-specific manner at 10°-25° C. or 20°-35° C. The test period extended over 2 to 4 weeks. During this time the plants were tended, and their reaction to the individual treatments was assessed.

The herbicidal action was assessed on a scale of from 0 to 100. 100 here means no emergence of the plants or complete destruction at least of the above-ground parts and 0 means no damage or normal course of growth.

The growth-regulating action was determined by height measurement. At the end of the test, the growth heights of the treated plants were measured and related to the growth heights of untreated plants.

The compound Nos. 2.262 and 1.156 according to the invention showed a good herbicidal action. 

We claim:
 1. A pyridine-N-oxide substituted salicylaldehyde or salicylic acid of the formula I ##STR24## where R is a group ##STR25## where R¹ has the following meanings: a) hydrogen;b) a succinylimidoxy group; c) a pyrrolyl, pyrazolyl, imidazolyl or triazolyl group linked via a nitrogen atom, which can carry one to two halogen atoms and/or one to two of the following radicals: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio; d) a radical --(O)_(m) --NR⁶ R⁷, where m is 0 or 1 and R⁶ and R⁷, which can be identical or different, have the following meanings: hydrogen;C₁ -C₈ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₃ -C₈ -cycloalkyl, these radicals in each case being able to carry one to five halogen atoms and/or one to two of the following groups: C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₄ -alkylthio, C₃ -C₆ -alkenylthio, C₃ -C₆ -alkynylthio, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylcarbonyl, C₃ -C₆ -alkenylcarbonyl, C₃ -C₆ -alkynylcarbonyl, C₁ -C₄ -alkoxycarbonyl, C₃ -C₆ -alkenyloxycarbonyl, C₃ -C₆ -alkynyloxycarbonyl, di-(C₁ -C₄ -alkyl)amino, C₃ -C₈ -cycloalkyl, phenyl or phenyl which is mono- or polysubstituted by halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio; phenyl, which can be substituted by one or more of the following radicals: halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio; R⁶ and R⁷ together are an unsubstituted or substituted C₄ -C₇ -alkylene chain closed to give a ring, selected from the group consisting of --(CH₂)₄ --, --(CH₂)₅ --, --(CH₂)₆ --, --(CH₂)₇, --CH₂ --CH═CH--CH₂ --, and --CH═CH--(CH₂)₃ -- or together are an unsubstituted or substituted C₃ -C₆ -alkylene chain which contains a heteroatom and is closed to give a ring, selected from the group consisting of --(CH₂)₂ --O--(CH₂)₂ --, --CH₂ --S--(CH₂)₃ --, --(CH₂)₂ --O--(CH₂)₃ --, --NH--(CH₂)₃, --CH--NH--(CH₂)₂ --; e) R¹ is additionally a group ##STR26## where R⁸ is C₁ -C₄ -alkyl, phenyl, phenyl which is mono- or polysubstituted by halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, p assumes the values 1, 2, 3 or 4 and k assumes the values 0, 1 or 2; f ) a radical OR⁹, where R⁹ is:i) hydrogen, an alkali metal cation, the equivalent of an alkaline earth metal cation, the ammonium cation or an organic ammonium ion; ii) a C₃ -C₈ -cycloalkyl group, which can carry one to three C₁ -C₄ -alkyl radicals; iii) a C₁ -C₈ -alkyl group, which can carry one to five halogen atoms and/or one of the following radicals:C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, cyano, C₁ -C₄ -alkylcarbonyl, C₃ -C₈ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, phenyl, or phenyl or phenoxy which is mono- or polysubstituted by halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio; iv) a C₁ -C₈ -alkyl group, which can carry one to five halogen atoms and carries one of the following radicals: a 5-membered heteroaromatic selected from the group consisting of pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, benzotriazolyl, isoxazolyl, oxazolyl and thiazolyl, bonded via a C atom or, if possible, an N atom, which can carry one to four halogen atoms and/or one to two of the following radicals: nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio; v) a C₂ -C₆ -alkyl group, which in the 2-position carries one of the following radicals: C₁ -C₄ -alkoxyimino, C₃ -C₆ -alkenyloxyimino, C₃ -C₆ -haloalkenyloxyimino or benzyloxyimino; vi) a C₃ -C₆ -alkenyl group or a C₃ -C₆ -alkynyl group, where these groups in turn can carry one to five halogen atoms; vii) a phenyl radical which can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio; viii) a 5-membered heteroaromatic selected from the group consisting of pyrazolyl, imidazolyl, benzimidazolyl, triazolyl and benzotriazolyl and linked via a nitrogen atom which can carry one to two halogen atoms and/or one to two of the following radicals: nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and/or C₁ -C₄ -alkylthio; ix) R⁹ is additionally a group --N═C--R¹⁰ R¹¹, where R¹⁰ and R¹¹, which can be identical or different, are:C₁ -C₁₂ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₃ -C₈ -cycloalkyl, these radicals being able to carry a C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio radical and/or a phenyl radical; phenyl which can be substituted by one or more of the following radicals: halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio; or R¹⁰ and R¹¹ together form a C₃ -C₁₂ -alkylene chain which can carry one to three C₁ -C₄ -alkyl groups; g) or R¹ forms a radical --NH--SO₂ R¹², where R¹² is:C₁ -C₄ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₃ -C₈ -cycloalkyl, these radicals being able to carry a C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio radical and/or a phenyl radical; phenyl which can be substituted by one or more of the following radicals: halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio; R² is halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio; X is CR¹³, R¹³ being hydrogen or halogen or together with R³ forming a 3- to 4-membered alkylene or alkenylene chain in which one methylene group in each case is replaced by oxygen, such chain selected from the group consisting of --CH₂ --CH₂ --O--, --CH═CH--O--, --CH₂ --CH₂ --CH₂ --O-- and --CH═CH--CH₂ --O--; R³ is halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio, or R³ is linked with R¹³ as indicated above to give a 5- or 6-membered ring; Y is oxygen or sulfur; R¹⁴ -R¹⁷ area) a C₃ -C₈ -cycloalkyl group, which can carry one to three C₁ -C₄ -alkyl radicals; b) a C₁ -C₈ -alkyl group, a C₁ -C₈ -alkoxy group or a C₁ -C₄ -alkylthio group, the groups mentioned in each case being able to carry one to five halogen atoms and/or one of the following radicals:C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, cyano, C₃ -C₈ -cycloalkyl or di-C₁ -C₄ -alkylamino; c) a di-C₁ -C₄ -alkylamino or a di-C₁ -C₄ -alkylaminoxy group; d) a C₂ -C₆ -alkenyl group or a C₂ -C₆ -alkynyl group, which can carry one to five halogen atoms and/or one of the following radicals:C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio; e) hydrogen, halogen, nitro or cyano.
 2. A pyridine-N-oxide-substituted derivative of the formula I as defined in claim 1 where X is CH.
 3. A pyridine-N-oxide-substituted salicylaldehyde or salicylic acid derivative of the formula I as defined in claim 1, where at least two of the radicals R¹⁵ to R¹⁷ are hydrogen.
 4. A pyridine-N-oxide-substituted salicylaldehyde or salicylic acid derivative of the formula I as defined in claim 1, where R³ is methoxy and X is CH or CF, or R³ is linked with X to give an --OCH₂ CH₂ -- chain.
 5. A pyridine-N-oxide-substituted salicylaldehyde or salicylic acid derivative of the formula I as defined in claim 1, where two of the radicals R¹⁴ to R¹⁷ are hydrogen and the remaining radical is a C₁ -C₄ -alkyl group.
 6. A process for preparing crop protection active compounds of the formula I' ##STR27## where R², R³, R¹⁴ -R¹⁷, X and Y have the meanings indicated in claim 1, and R¹ has the meanings indicated in claim 1, with the exception of hydrogen, the succinylimidoxy group and of those radicals OR⁹ where R⁹ is hydrogen, an alkali metal cation, the equivalent of an alkaline earth metal cation, the ammonium cation or an organic ammonium ion, which process comprises: reacting a compound of the formula IV ##STR28## first with a salt R¹ M, M being an alkali metal cation or an equivalent of an alkaline earth metal cation, and then with a heterocycle of the formula V ##STR29## where R⁴ is halogen, alkylsulfonyl, haloalkylsulfonyl or an equivalent leaving group, in an inert solvent.
 7. A herbicidal composition or composition for influencing plant growth, which contains one or more pyridine-N-oxide-substituted salicylaldehyde or salicylic acid derivative of the formula I as defined in claim 1 and inert carriers.
 8. A process for controlling undesired plant growth and for influencing plant growth, which comprises allowing a herbicidally active amount of a pyridine-N-oxide-substituted salicylaldehyde or salicylic acid derivative of the formula I as defined in claim 1 to act on the plants and/or their environment. 